Phenyl-substituted 5,6-dihydrophyne derivatives for use as pesticides and herbicides

ABSTRACT

The present invention relates to novel phenyl-substituted 5,6-dihydro-pyrone derivatives of the formula (I)  
                 
 
     in which  
     W, X, Y, Z, G, A, B, Q 1  and Q 2  are each as defined in the description,  
     to a plurality of processes for their preparation and to their use as pesticides and herbicides.

[0001] The present invention relates to novel phenyl-substituted5,6-dihydro-pyrone derivatives, to a plurality of processes for theirpreparation and to their use as pesticides and herbicides.

[0002] It is known that certain 5,6-dihydropyrone derivatives have, asprotease inhibitors, antiviral properties: WO 95/14012. Furthermore,4-phenyl-6-(2-phenethyl)-5,6-dihydropyrone is known from the synthesisof kavalactone derivatives: Kappe et al.; Arch. Pharm. 309, 558-64,(1976). Moreover, 5,6-dihydropyrone derivatives are known asintermediates: White, J. D., Brenner, J. B., Deinsdale, M. J., J. Amer.Chem. Soc. 93, 281-2 (1971). Applications in crop protection havehitherto not been described.

[0003] This invention now provides novel compounds of the formula (I)

[0004] in which

[0005] W represents hydrogen, alkyl, alkenyl, alkinyl, halogen,halogenoalkyl or alkoxy,

[0006] X represents halogen, alkyl, alkoxy, alkenyl, alkinyl,halogenoalkyl, halogenoalkoxy, cyano or in each case optionallysubstituted phenyl, phenoxy, phenylthio, phenylalkoxy orphenylalkylthio,

[0007] Y represents hydrogen, alkyl, halogen, halogenoalkyl, alkoxy,alkenyl, alkinyl or optionally substituted aryl or hetaryl,

[0008] Z represents hydrogen, halogen, alkyl, alkoxy, halogenoalkyl,halogenoalkoxy or cyano,

[0009] A represents a bond, hydrogen, in each case optionallyhalogen-substituted alkyl, alkenyl, alkoxyalkyl, optionally substitutedcycloalkyl or cycloalkylalkyl in which optionally at least one ring atomis replaced by a hetero atom, or in each case optionally halogen-,alkyl-, halogenoalkyl-, alkoxy-, halogenoalkoxy-, cyano- ornitro-substituted aryl, arylalkyl, hetaryl or hetarylalkyl,

[0010] B represents hydrogen or alkyl, or

[0011] A and B together with the carbon atom to which they are attachedrepresent a saturated or unsaturated unsubstituted or substituted cyclewhich optionally contains at least one hetero atom, or

[0012] B and Q¹ together represent alkanediyl which is optionallysubstituted by in each case optionally substituted alkyl or alkoxy andin which two not directly adjacent carbon atoms optionally form afurther optionally substituted cycle or

[0013] Q¹ represents hydrogen, hydroxyl, alkyl, alkoxy, alkoxyalkyl,alkylacyloxy, optionally substituted cycloalkyl (in which optionally onemethylene group is replaced by oxygen or sulphur) or optionallysubstituted phenyl,

[0014] Q² represents hydrogen or alkyl, or

[0015] Q¹ and Q² together with the carbon atom to which they areattached represent an unsubstituted or substituted cycle whichoptionally contains a hetero atom,

[0016] G represents hydrogen (a) or represents one of the groups

[0017] in which

[0018] E represents a metal ion or an ammonium ion,

[0019] L represents oxygen or sulphur,

[0020] M represents oxygen or sulphur,

[0021] R¹ represents in each case optionally halogen-substituted alkyl,alkenyl, alkoxyalkyl, alkylthioalkyl, polyalkoxyalkyl or optionallyhalogen-, alkyl- or alkoxy-substituted cycloalkyl in which one or moremethylene groups may be replaced by hetero atoms, in each caseoptionally substituted phenyl, phenylalkyl, hetaryl, phenoxyalkyl orhetaryloxyalkyl,

[0022] R² represents in each case optionally halogen-substituted alkyl,alkenyl, alkoxyalkyl, polyalkoxyalkyl or represents in each caseoptionally substituted cycloalkyl, phenyl or benzyl,

[0023] R³, R⁴ and R⁵ independently of one another each represent in eachcase optionally halogen-substituted alkyl, alkoxy, alkylamino,dialkylamino, alkylthio, alkenylthio, cycloalkylthio and represent ineach case optionally substituted phenyl, benzyl, phenoxy or phenylthio,and

[0024] R⁶ and R⁷ independently of one another each represent hydrogen,in each case optionally halogen-substituted alkyl, cycloalkyl, alkenyl,alkoxy, alkoxyalkyl, represent optionally substituted phenyl, representoptionally substituted benzyl, or together with the N atom to which theyare attached represent a ring which is optionally interrupted by oxygenor sulphur.

[0025] Depending inter alia on the nature of the substituents, thecompounds of the formula (I) can be present as geometrical and/oroptical isomers or isomer mixtures of varying composition which, ifrequired, can be separated in a customary manner. The invention providesboth the pure isomers and the isomer mixtures, their preparation anduse, and compositions comprising them. Hereinbelow, for the sake ofsimplicity, only compounds of the formula (I) are referred to, althoughthis may mean both the pure compounds and, if appropriate, also mixturescontaining different percentages of isomeric compounds.

[0026] Depending on the position of the substituent G, the compounds ofthe formula (I) can be present in the two isomeric forms of the formulae(I-A) and (I-B)

[0027] which is meant to be indicated by the broken line in formula (I).

[0028] The compounds of the formulae (I-A) and (I-B) can be presenteither as mixtures or in the form of their pure isomers. Mixtures of thecompounds of the formulae (I-A) and (I-B) can, if required, be separatedin a manner known per se by physical methods, for example bychromatographic methods.

[0029] For reasons of clarity, only one of the possible isomers is shownhereinbelow. This does not exclude that the compounds may, ifappropriate, be present in the form of the isomer mixtures or therespective other isomeric form.

[0030] Including the different meanings (a), (b), (c), (d), (e), (f) and(g) of group G, the following principal structures (I-a) to (I-g)result:

[0031] in which

[0032] A, B, E, L, M, Q¹, Q², W, X, Y, Z, R¹, R², R³, R⁴, R⁵, R⁶ and R⁷are each as defined above.

[0033] Furthermore, it has been found that the novel compounds of theformula (I) can be obtained by one of the processes described below:

[0034] (A) substituted 5,6-dihydropyrones of the formula (I-a)

[0035] in which

[0036] A, B, Q¹, Q², W, X, Y and Z are each as defined above, can beobtained when

[0037] O-acylhydroxycarboxylic esters of the formula (II)

[0038] in which

[0039] A, B, Q¹, Q², W, X, Y and Z are each as defined above,

[0040] and

[0041] R⁸ represents alkyl (preferably C₁-C₆-alkyl),

[0042] are condensed intramolecularly in the presence of a diluent andin the presence of a base.

[0043] Furthermore, it has been found

[0044] (B) that compounds of the formulae (I-a) to (I-g) shown above inwhich A, B, G, Q¹, Q², W, X, Y and Z are each as defined above areobtained when compounds of the formulae (I-a′) to (I-g′),

[0045] in which

[0046] A, B, R¹, R², R³, R⁴, R⁵, R⁶, R⁷, E, L, M, Q¹, Q², W′, X′, Y′ andZ′ each have the meanings of W, X, Y and Z given above and where atleast one of the radicals

[0047] W′, X′, Y′ represents chlorine, bromine or iodine, preferablybromine,

[0048] and Z′ does not represent bromine or iodine,

[0049] α) are initially reacted with silylacetylene of the formula (III)

[0050] in which

[0051] R⁹ represents hydrogen and

[0052] R¹⁰ represents C₁-C₄-alkyl or phenyl, in particular methyl ortert-butyl,

[0053] in the presence of a solvent, a base and a catalyst, suitablecatalysts being, in particular, palladium complexes, and the silyl groupis subsequently removed,

[0054] or

[0055] β) are reacted with vinylstannanes of the formula (IV)

[0056] in which

[0057] R⁹ represents hydrogen, methyl or ethyl and

[0058] R¹⁰ represents C₁-C₄-alkyl, in particular butyl,

[0059] in the presence of a solvent, if appropriate in the presence of abase and in the presence of a catalyst, suitable catalysts being, inparticular, palladium complexes,

[0060] or

[0061] γ) in the specific case where Y′ represents chlorine, bromine oriodine, preferably bromine, and W′, X′ and Z′ do not represent bromineor iodine, are reacted with boronic acids of the formula (V)

[0062] in which

[0063] Y represents optionally substituted phenyl or hetaryl,

[0064] in the presence of a solvent, a base and a catalyst, suitablecatalysts being, in particular, palladium complexes.

[0065] Moreover, it has been found

[0066] (C) that the compounds of the formula (I-b) shown above in whichA, B, Q¹, Q², R¹, W, X, Y and Z are each as defined above are obtainedwhen compounds of the formula (I-a) shown above in which A, B, Q¹, Q²,W, X, Y and Z are each as defined above are in each case reacted

[0067] (α) with acyl halides of the formula (VI)

[0068] in which

[0069] R¹ is as defined above and

[0070] Hal represents halogen (in particular chlorine or bromine)

[0071] or

[0072] (β) with carboxylic anhydrides of the formula (VII)

R¹—CO—O—CO—R¹   (VII)

[0073] in which

[0074] R¹ is as defined above,

[0075] if appropriate in the presence of a diluent and if appropriate inthe presence of an acid binder;

[0076] (D) that the compounds of the formula (I-c) shown above in whichA, B, Q¹, Q², R², M, W, X, Y and Z are each as defined above and Lrepresents oxygen are obtained when the compounds of the formula (I-a)shown above in which A, B, Q¹, Q², W, X, Y and Z are each as definedabove are in each case reacted

[0077] with chloroformic esters or chloroformic thioesters of theformula (VIII)

R²-M-CO—Cl   (VIII)

[0078] in which

[0079] R² and M are each as defined above,

[0080] if appropriate in the presence of a diluent and if appropriate inthe presence of an acid binder;

[0081] (E) that compounds of the formula (I-c) shown above in which A,B, Q¹, Q², R², M, W, X, Y and Z are each as defined above and Lrepresents sulphur are obtained when compounds of the formula (I-a)shown above in which A, B, Q¹, Q², W, X, Y and Z are each as definedabove are in each case reacted

[0082] with chloromonothioformic esters or chlorodithioformic esters ofthe formula (IX)

[0083] in which

[0084] M and R² are each as defined above,

[0085] if appropriate in the presence of a diluent and if appropriate inthe presence of an acid binder,

[0086] and

[0087] (F) that compounds of the formula (I-d) shown above in which A,B, Q¹, Q², R³, W, X, Y and Z are each as defined above are obtained whencompounds of the formula (I-a) shown above in which A, B, Q¹, Q², W, X,Y and Z are each as defined above are in each case reacted

[0088] with sulphonyl chlorides of the formula (X)

R³—SO₂—Cl   (X)

[0089] in which

[0090] R³ is as defined above,

[0091] if appropriate in the presence of a diluent and if appropriate inthe presence of an acid binder,

[0092] (G) that compounds of the formula (I-e) shown above in which A,B, L, Q¹, Q², R⁴, R⁵, W, X, Y and Z are each as defined above areobtained when compounds of the formula (I-a) shown above in which A, B,Q¹, Q², W, X, Y and Z are each as defined above are in each case reacted

[0093] with phosphorus compounds of the formula (XI)

[0094] in which

[0095] L, R⁴ and R⁵ are each as defined above and

[0096] Hal represents halogen (in particular chlorine or bromine),

[0097] if appropriate in the presence of a diluent and if appropriate inthe presence of an acid binder,

[0098] (H) that compounds of the formula (I-f) shown above in which A,B, E, Q¹, Q², W, X, Y and Z are each as defined above are obtained whencompounds of the formula (I-a) shown above in which A, B, Q¹, Q², W, X,Y and Z are each as defined above are in each case reacted

[0099] with metal compounds or amines of the formula (XII) or (XIII)

Me(OR¹¹)_(t)   (XII)

[0100] in which

[0101] Me represents a mono- or divalent metal (preferably an alkalimetal or alkaline earth metal such as lithium, sodium, potassium,magnesium or calcium),

[0102] t represents the number 1 or 2 and

[0103] R¹¹, R¹², R¹³ independently of one another each representhydrogen or alkyl (preferably C₁-C₈-alkyl),

[0104] if appropriate in the presence of a diluent,

[0105] (I) that compounds of the formula (I-g) show above in which A, B,L, Q¹, Q², R⁶, R⁷, W, X, Y and Z are each as defined above are obtainedwhen compounds of the formula (I-a) shown above in which A, B, Q¹, Q²,W, X, Y and Z are each as defined above are in each case

[0106] (α) reacted with isocyanates or isothiocyanates of the formula(XIV)

R⁶—N═C=L   (XIV)

[0107] in which

[0108] R⁶ and L are each as defined above,

[0109] if appropriate in the presence of a diluent and if appropriate inthe presence of a catalyst or

[0110] (β) are reacted with carbamoyl chlorides or thiocarbamoylchlorides of the formula (XV)

[0111] in which

[0112] L, R⁶ and R⁷ are each as defined above,

[0113] if appropriate in the presence of a diluent and if appropriate inthe presence of an acid binder.

[0114] Furthermore, it has been found that 5,6-dihydropyrone derivativesof the formula (I) can be prepared by reacting

[0115] J) silyl enol ethers of the formula

[0116] in which

[0117] A and B are each as defined above and

[0118] Alk represents alkyl having 1 to 4 carbon atoms,

[0119] in each case with ketene derivatives of the formula

[0120] in which

[0121] W, X, Y and Z are each as defined above and

[0122] Hal represents chlorine or bromine,

[0123] if appropriate in the presence of a diluent or a diluent mixtureand if appropriate in the presence of an acid binder.

[0124] Furthermore, it has been found that the novel compounds of theformula (I) have very good activity as pesticides, preferably asinsecticides, acaricides and also as herbicides.

[0125] The formula (I) provides a general definition of the compoundsaccording to the invention. Preferred substituents or ranges of theradicals listed in the formulae mentioned above and below areillustrated below:

[0126] W preferably represents hydrogen, C₁-C₆-alkyl, C₂-C₄-alkenyl,ethinyl, fluorine, chlorine, bromine, C₁-C₄-halogenoalkyl orC₁-C₆-alkoxy,

[0127] X preferably represents fluorine, chlorine, bromine, C₁-C₆-alkyl,C₁-C₄-halogenoalkyl, C₁-C₆-alkoxy, C₂-C₄-alkenyl, ethinyl,C₁-C₄-halogenoalkoxy, cyano or in each case optionally halogen-,C₁-C₆-alkyl-, C₁-C₆-alkoxy-, C₁-C₄-halogenoalkyl-,C₁-C₄-halogenoalkoxy-, nitro- or cyano-substituted phenyl or benzyloxy,

[0128] Y preferably represents hydrogen, C₁-C₆-alkyl,C₁-C₄-halogenoalkyl, fluorine, chlorine, bromine, C₁-C₆-alkoxy,C₂-C₄-alkenyl, ethinyl or represents one of the radicals

[0129] V¹ preferably represents hydrogen, halogen, C₁-C₁₂-alkyl,C₁-C₆-alkoxy, C₁-C₆-alkylthio, C₁-C₄-halogenoalkyl,C₁-C₄-halogenoalkoxy, nitro, cyano or represents phenyl, phenoxy,phenoxy-C₁-C₄-alkyl, phenyl-C₁-C₄-alkoxy, phenylthio-C₁-C₄-alkyl orphenyl-C₁-C₄-alkylthio, each of which is optionally mono- orpolysubstituted by halogen, C₁-C₆-alkyl, C₁-C₆-alkoxy,C₁-C₄-halogenoalkyl, C₁-C₄-halogenoalkoxy, nitro or cyano,

[0130] V² preferably represents hydrogen, fluorine, chlorine,C₁-C₆-alkyl, C₁-C₆-alkoxy, C₁-C₄-halogenoalkyl or C₁-C₄-halogenoalkoxy,

[0131] V³ preferably represents hydrogen, fluorine, chlorine, methyl ormethoxy,

[0132] Z preferably represents hydrogen, fluorine, chlorine, bromine,C₁-C₆-alkyl, C₁-C₄-halogenoalkyl, C₁-C₆-alkoxy, C₁-C₄-halogenoalkoxy orcyano,

[0133] with the first proviso, that W, X and Z do not represent bromine,C₂-C₄-alkenyl and ethinyl if Y represents V¹-, V²- and V³-substitutedphenyl or hetaryl and that secondly only at most two of the radicals W,X and Y represent C₂-C₄-alkenyl or ethinyl, with the proviso that noneof the other radicals W, X, Y and Z may represent bromine,

[0134] A preferably represents a bond, hydrogen or in each caseoptionally halogen-substituted C₁-C₁₂-alkyl, C₃-C₈-alkenyl,C₁-C₆-alkoxy-C₁-C₄-alkyl, in each case optionally halogen-, C₁-C₄-alkyl-or C₁-C₄-alkoxy-substituted C₃-C₈-cycloalkyl orC₃-C₆-cycloalkyl-C₁-C₄-alkyl in which optionally one or two not directlyadjacent ring members are replaced by oxygen and/or sulphur orrepresents in each case optionally halogen-, C₁-C₆-alkyl-,C₁-C₆-halogenoalkyl-, C₁-C₆-alkoxy-, C₁-C₆-halogenoalkoxy-, cyano- ornitro-substituted phenyl, benzyl, hetaryl having 5 or 6 ring atoms (forexample furanyl, pyridyl, imidazolyl, triazolyl, pyrazolyl, pyrimidyl,thiazolyl or thienyl) or hetaryl-C₁-C₄-alkyl having 5 or 6 ring atoms(for example pyridyl, pyrimidyl or thiazolyl),

[0135] B preferably represents hydrogen or C₁-C₆-alkyl, or

[0136] A, B and the carbon atom to which they are attached preferablyrepresent saturated C₃-C₁₀-cycloalkyl or unsaturated C₅-C₁₀-cycloalkylin which optionally one ring member is replaced by oxygen or sulphur andwhich are optionally mono- or disubstituted by C₁-C₆-alkyl,C₃-C₈-cycloalkyl, C₁-C₆-halogenoalkyl, C₁-C₆-alkoxy, C₁-C₆-alkylthio,halogen or phenyl, with the proviso that Q¹ and Q² do not form a furthercycle, or

[0137] B and Q¹ together preferably represent C₃-C₆-alkanediyl which isoptionally mono- or disubstituted by identical or different C₁-C₄-alkyland in which two not directly adjacent carbon atoms optionally form afurther 3- to 6-membered cycle, or

[0138] Q¹ preferably represents hydrogen, hydroxyl, C₁-C₆-alkyl,C₁-C₆-alkoxy, C₁-C₆-alkoxy-C₁-C₂-alkyl, C₁-C₆-alkylacyloxy, optionallyfluorine-, chlorine-, C₁-C₄-alkyl-, C₁-C₂-halogenoalkyl- orC₁-C₄-alkoxy-substituted C₃-C₈-cycloalkyl in which optionally onemethylene group is replaced by oxygen or sulphur or optionally halogen,C₁-C₄-alkyl-, C₁-C₄-alkoxy-, C₁-C₂-halogenoalkyl-,C₁-C₂-halogenoalkoxy-, cyano- or nitro-substituted phenyl,

[0139] Q² preferably represents hydrogen or C₁-C₄-alkyl, or

[0140] Q¹ and Q² together with the carbon atom to which they areattached preferably represent optionally C₁-C₆-alkyl-, C₁-C₆-alkoxy- orC₁-C₂-halogenoalkyl-substituted C₃-C₇-cycloalkyl in which optionally onering member is replaced by oxygen or sulphur, with the proviso that Aand B do not form a further cycle,

[0141] G represents hydrogen (a) or represents one of the groups

[0142] E (f) or

[0143] in particular (a), (b) or (c),

[0144] in which

[0145] E represents a metal ion or an ammonium ion,

[0146] L represents oxygen or sulphur and

[0147] M represents oxygen or sulphur.

[0148] R¹ preferably represents in each case optionallyhalogen-substituted C₁-C₂₀-alkyl, C₂-C₂₀-alkenyl,C₁-C₈-alkoxy-C₁-C₈-alkyl, Cl -C₈-alkylthio-C₁-C₈-alkyl,poly-C₁-C₈-alkoxy-C₁-C₈-alkyl or optionally halogen-, C₁-C₆-alkyl- orC₁-C₆-alkoxy-substituted C₃-C₈-cycloalkyl in which optionally one ormore (preferably one or two) not directly adjacent ring members arereplaced by oxygen and/or sulphur, or

[0149] represents optionally halogen-, cyano-, nitro-, C₁-C₆-alkyl-,C₁-C₆-alkoxy-, C₁-C₆-halogenoalkyl-, C₁-C₆-halogenoalkoxy-,C₁-C₆-alkylthio- or C₁-C₆-alkylsulphonyl-substituted phenyl, or

[0150] represents optionally halogen-, nitro-, cyano-, C₁-C₆-alkyl-,C₁-C₆-alkoxy-, C₁-C₆-halogenoalkyl- or C₁-C₆-halogenoalkoxy-substitutedphenyl-C₁-C₆-alkyl, or

[0151] represents optionally halogen-, C₁-C₆-alkyl- ortrifluoromethyl-substituted 5- or 6-membered hetaryl (for examplepyrazolyl, thiazolyl, pyridyl, pyrimidyl, furanyl or thienyl), or

[0152] represents optionally halogen- or C₁-C₆-alkyl-substitutedphenoxy-C₁-C₆-alkyl or

[0153] represents optionally halogen-, amino- or C₁-C₆-alkyl-substituted5- or 6-membered hetaryloxy-C₁-C₆-alkyl (for examplepyridyloxy-C₁-C₆-alkyl, pyrimidyloxy-C₁-C₆-alkyl orthiazolyloxy-C₁-C₆-alkyl),

[0154] R² preferably represents in each case optionallyhalogen-substituted C₁-C₂₀-alkyl, C₂-C₂₀-alkenyl,C₁-C₈-alkoxy-C₂-C₈-alkyl, poly-C₁-C₈-alkoxy-C₂-C₈-alkyl, or

[0155] represents optionally halogen-, C₁-C₆-alkyl- orC₁-C₆-alkoxy-substituted C₃-C₈-cycloalkyl or

[0156] represents in each case optionally halogen-, cyano-, nitro-,C₁-C₆-alkyl-, C₁-C₆-alkoxy-, C₁-C6-halogenoalkyl- orC₁-C₆-halogenoalkoxy-substituted phenyl or benzyl,

[0157] R³ preferably represents optionally halogen-substitutedC₁-C₈-alkyl or represents in each case optionally halogen-,C₁-C₆-alkyl-, C₁-C₆-alkoxy-, C₁-C₄-halogenoalkyl-,C₁-C₄-halogenoalkoxy-, cyano- or nitro-substituted phenyl or benzyl,

[0158] R⁴ and R⁵ independently of one another each preferably representin each case optionally halogen-substituted C₁-C₈-alkyl, C₁-C₈-alkoxy,C₁-C₈-alkylamino, di-(C₁-C₈-alkyl)amino, C₁-C₈-alkylthio,C₂-C₈-alkenylthio, C₃-C₇-cycloalkylthio or represent in each caseoptionally halogen-, nitro-, cyano-, C₁-C₄-alkoxy-,C₁-C₄-halogenoalkoxy-, C₁-C₄-alkylthio-, C₁-C₄-halogenoalkylthio-,C₁-C₄-alkyl- or C₁-C₄-halogenoalkyl-substituted phenyl, benzyl, phenoxyor phenylthio,

[0159] R⁶ and R⁷ independently of one another each preferably representhydrogen, represent in each case optionally halogen-substitutedC₁-C₈-alkyl, C₃-C₈-cycloalkyl, C₁-C₈-alkoxy, C₃-C₈-alkenyl,C₁-C₈-alkoxy-C₁-C₈-alkyl, represent optionally halogen-,C₁-C₈-halogenoalkyl-, C₁-C₈-alkyl- or C₁-C₈-alkoxy-substituted phenyl,optionally halogen-, C₁-C₈-alkyl-, C₁-C₈-halogenoalkyl- orC₁-C₈-alkoxy-substituted benzyl or together represent an optionallyC₁-C₄-alkyl-substituted C₃-C₆-alkylene radical in which optionally onecarbon atom is replaced by oxygen or sulphur.

[0160] In the radical definitions mentioned as being preferred, halogen,also as substituent such as, for example, in halogenoalkyl, representsfluorine, chlorine, bromine and iodine, in particular fluorine andchlorine.

[0161] W particularly preferably represents hydrogen, C₁-C₄-alkyl,chlorine or bromine,

[0162] X particularly preferably represents chlorine, bromine,C₁-C₄-alkyl, C₁-C₄-alkoxy, C₂-C₃-alkenyl, ethinyl, C₁-C₂-halogenoalkyl,C₁-C₂-halogenoalkoxy or cyano,

[0163] Y particularly preferably represents hydrogen, C₁-C₄-alkyl,C₁-C₂-halogenoalkyl, fluorine, chlorine, bromine, C₁-C₄-alkoxy,C₂-C₃-alkenyl, ethinyl, 2-thienyl, 3-thienyl or represents the radical

[0164] V¹ particularly preferably represents hydrogen, fluorine,chlorine, bromine, C₁-C₆-alkyl, C₁-C₄-alkoxy, C₁-C₄-alkylthio,C₁-C₂-halogenoalkyl, C₁-C₂-halogenoalkoxy, nitro, cyano or phenyl,

[0165] V² particularly preferably represents hydrogen, fluorine,chlorine, C₁-C₄-alkyl, C₁-C₄-alkoxy or C₁-C₂-halogenoalkyl,

[0166] Z particularly preferably represents hydrogen, fluorine,chlorine, bromine, C₁-C₄-alkyl, C₁-C₂-halogenoalkyl, C₁-C₄-alkoxy orC₁-C₂-halogenoalkoxy,

[0167] with the first proviso that W, X and Z do not represent bromine,C₂-C₃-alkenyl and ethinyl if Y represents V¹- and V²-substituted phenyl,2-thienyl or 3-thienyl and that secondly only one of the radicals X andY represents C₂-C₃-alkenyl and ethinyl, with the proviso that in thiscase none of the other radicals W, X, Y and Z may represent bromine,

[0168] A particularly preferably represents a bond, hydrogen, in eachcase optionally fluorine-substituted C₁-C₈-alkyl,C₁-C₄-alkoxy-C₁-C₂-alkyl, in each case optionally fluorine-, chlorine-,methyl-, ethyl- or methoxy-substituted C₅-C₆-cycloalkyl orC₃-C₆-cycloalkyl-C₁-C₂-alkyl in which optionally one ring member isreplaced by oxygen or sulphur or in each case optionally fluorine-,chlorine-, bromine-, C₁-C₄-alkyl-, C₁-C₂-halogenoalkyl-, C₁-C₄-alkoxy-or C₁-C₂-halogenoalkoxy-substituted phenyl or benzyl,

[0169] B particularly preferably represents hydrogen or C₁-C₄-alkyl, or

[0170] A, B and the carbon atom to which they are attached particularlypreferably represent saturated C₅-C₇-cycloalkyl in which optionally onering member is replaced by oxygen and which is optionallymonosubstituted by C₁-C₄-alkyl, trifluoromethyl or C₁-C₄-alkoxy, withthe proviso that Q¹ and Q² do not form a further cycle, or

[0171] B and Q¹ together particularly preferably representC₃-C₄-alkanediyl which is optionally monosubstituted by C₁-C₂-alkyl andin which two not directly adjacent carbon atoms optionally form afurther five- or six-membered cycle, or

[0172] Q¹ particularly preferably represents hydrogen, hydroxyl,C₁-C₄-alkyl, C₁-C₄-alkoxy, C₁-C₄-alkoxy-C₁-C₂-alkyl, C₁-C₄-alkylacyloxyor optionally methyl- or methoxy-substituted C₃-C₆-cycloalkyl in whichoptionally one methylene group is replaced by oxygen,

[0173] Q² particularly preferably represents hydrogen, methyl or ethyl,or

[0174] Q¹ and Q² particularly preferably together with the carbon towhich they are attached represent optionally C₁-C₄-alkyl-,trifluoromethyl- or C₁-C₄-alkoxy-substituted saturated C₅-C₆-cycloalkylin which optionally one ring member is replaced by oxygen, with theproviso that A and B do not form a further cycle,

[0175] G particularly preferably represents hydrogen (a) or representsone of the groups

[0176] E (f) or

[0177] in particular (a), (b) or (c),

[0178] in which

[0179] E represents a metal ion or an ammonium ion,

[0180] L represents oxygen or sulphur and

[0181] M represents oxygen or sulphur,

[0182] R¹ particularly preferably represents in each case optionallyfluorine- or chlorine-substituted C₁-C₁₆-alkyl, C₂-C₁₆-alkenyl,C₁-C₄-alkoxy-C₁-C₂-alkyl, C₁-C₄-alkylthio-C₁-C₂-alkyl, or optionallyfluorine-, chlorine-, C₁-C₂-alkyl-, or

[0183] C₁-C₂-alkoxy-substituted C₃-C₇-cycloalkyl in which optionally oneor two not directly adjacent ring members are replaced by oxygen and/orsulphur, or

[0184] represents phenyl which is optionally mono- or disubstituted byfluorine, chlorine, bromine, cyano, nitro, C₁-C₄-alkyl, C₁-C₄-alkoxy,trifluoromethyl or trifluoromethoxy, or

[0185] represents pyridyl or thienyl, each of which is optionallymonosubstituted by fluorine, chlorine, bromine, methyl, ethyl ortrifluoromethyl,

[0186] R² particularly preferably represents C₁-C₁₆-alkyl,C₂-C₁₆-alkenyl or C₁-C₄-alkoxy-C₂-C₄-alkyl, each of which is optionallymono- to trisubstituted by fluorine, or

[0187] represents C₃-C₇-cycloalkyl which is optionally monosubstitutedby methyl, ethyl or methoxy, or

[0188] represents phenyl or benzyl, each of which is optionally mono- ordisubstituted by fluorine, chlorine bromine, cyano, nitro, C₁-C₄-alkyl,C₁-C₃-alkoxy, trifluoromethyl or trifluoromethoxy,

[0189] R³ particularly preferably represents C₁-C₆-alkyl which isoptionally mono- to pentasubstituted by fluorine or represents phenylwhich is optionally mono- or disubstituted by fluorine, chlorine,bromine, C₁-C₄-alkyl, C₁-C₄-alkoxy, trifluoromethyl, trifluoromethoxy,cyano or nitro,

[0190] R⁴ particularly preferably represents C₁-C₆-alkyl, C₁-C₆-alkoxy,C₁-C₆-alkylamino, di-(C₁-C₆-alkyl)amino, C₁-C₆-alkylthio, or representsphenyl, benzyl, phenoxy or phenylthio, each of which is optionally mono-or disubstituted by fluorine, chlorine, bromine, nitro, cyano,C₁-C₃-alkoxy, trifluoromethoxy, C₁-C₃-alkyl or trifluoromethyl,

[0191] R⁵ particularly preferably represents C₁-C₄-alkyl, C₁-C₄-alkoxyor C₁-C₄-alkylthio,

[0192] R⁶ particularly preferably represents C₁-C₆-alkyl,C₃-C₆-cycloalkyl, C₁-C₆-alkoxy, C₃-C₆-alkenyl, C₁-C₆-alkoxy-C₁-C₆-alkyl,or represents phenyl which is optionally mono- or disubstituted byfluorine, chlorine, bromine, trifluoromethyl, C₁-C₄-alkyl orC₁-C₄-alkoxy, or represents benzyl which is optionally mono- ordisubstituted by fluorine, chlorine, bromine, methyl, ethyl,trifluoromethyl or methoxy,

[0193] R⁷ particularly preferably represents hydrogen, C₁-C₆-alkyl orC₃-C₆-alkenyl, or

[0194] R⁶ and R⁷ together particularly preferably represent aC₄-C₅-alkylene radical which is optionally mono- or disubstituted bymethyl or ethyl and in which optionally one methylene group is replacedby oxygen or sulphur.

[0195] In the radical definitions mentioned as being particularlypreferred, halogen, also as substituent, such as, for example, inhalogenoalkyl, represents fluorine, chlorine, bromine and iodine, inparticular fluorine or chlorine, particularly preferably fluorine.

[0196] W very particularly preferably represents hydrogen, chlorine,bromine, methyl or ethyl,

[0197] X very particularly preferably represents chlorine, bromine,methyl, ethyl, n-propyl, methoxy, ethoxy, trifluoromethyl,difluoromethoxy, trifluoromethoxy or cyano (especially chlorine,bromine, methyl, ethyl, n-propyl or trifluoromethyl),

[0198] Y very particularly preferably represents hydrogen, methyl,ethyl, propyl, iso-propyl, trifluoromethyl, fluorine, chlorine, bromine,methoxy or represents the radical

[0199] V¹ very particularly preferably represents hydrogen, fluorine,chlorine, bromine, methyl, ethyl, iso-propyl, tert-butyl, methoxy,trifluoromethyl or trifluoromethoxy cyano or phenyl,

[0200] V² very particularly preferably represents hydrogen, fluorine,chlorine, methyl or trifluoromethyl,

[0201] Z very particularly preferably represents hydrogen, fluorine,chlorine, bromine, methyl, methoxy or trifluoromethyl (especiallyhydrogen, fluorine, chlorine, bromine or methyl), with the proviso thatW, X and Z do not represent bromine if Y represents V¹- andV²-substituted phenyl,

[0202] A very particularly preferably represents a bond, hydrogen,methyl, ethyl, n-propyl, iso-propyl, n-butyl or iso-butyl,

[0203] B very particularly preferably represents hydrogen, methyl orethyl, or

[0204] A, B and the carbon atoms to which they are attached veryparticularly preferably represent saturated C₅-C₆-cycloalkyl in whichoptionally one ring member is replaced by oxygen and which is optionallymonosubstituted by methyl, ethyl, methoxy or ethoxy, with the provisothat Q¹ and Q² do not form a further cycle or

[0205] B and Q¹ together very particularly preferably representC₃-C₄-alkanediyl which is optionally monosubstituted by methyl and inwhich two not directly adjacent carbon atoms optionally form a furtherthree- to six-membered cycle, or

[0206] Q¹ very particularly preferably represents hydrogen, hydroxyl,methyl, ethyl, n-propyl, iso-propyl, methoxy, ethoxy, propoxy, acetyloxyor propionyloxy,

[0207] Q² very particularly preferably represents hydrogen, methyl orethyl, or

[0208] Q¹ and Q² together with the carbon to which they are attachedvery particularly preferably represent saturated C₆-cycloalkyl which isoptionally substituted by methyl, ethyl, methoxy, ethoxy, propoxy orbutoxy and in which optionally one ring member is replaced by oxygen,with the proviso that A and B do not form a further cycle,

[0209] G very particular preferably represents hydrogen (a) orrepresents one of the groups

[0210] E (f) or

[0211] in particular (a), (b) or (c),

[0212] in which

[0213] E represents a metal ion or an ammonium ion,

[0214] L represents oxygen (particularly preferably in the case of (c))or sulphur and

[0215] M represents oxygen or sulphur,

[0216] R¹ very particularly preferably represents in each caseoptionally fluorine- or chlorine-substituted C₁-C₈-alkyl, C₂-C₈-alkenyl,C₁-C₂-alkoxy-C₁-alkyl, C₁-alkylthio-C₁-alkyl, cyclopropyl, cyclopentylor cyclohexyl or

[0217] represents phenyl which is optionally monosubstituted byfluorine, chlorine, bromine, cyano, nitro, methyl, ethyl, iso-propyl,tert-butyl, methoxy, trifluoromethyl or trifluoromethoxy, or

[0218] represents thienyl or pyridyl, each of which is optionallymonosubstituted by chlorine, bromine or methyl,

[0219] R² very particularly preferably represents C₁-C₈-alkyl,C₂-C₈-alkenyl or C₁-C₄-alkoxy-C₂-alkyl, or cyclohexyl

[0220] or represents phenyl or benzyl, each of which is optionallymonosubstituted by fluorine, chlorine, bromine, cyano, nitro, methyl,tert-butyl, methoxy, trifluoromethyl or trifluoromethoxy,

[0221] R³ very particularly preferably represents methyl, ethyl,n-propyl, or phenyl which is optionally monosubstituted by fluorine,chlorine, bromine, methyl, tert-butyl, methoxy, trifluoromethyl,trifluoromethoxy, cyano or nitro,

[0222] R⁴ very particularly preferably represents C₁-C₄-alkyl,C₁-C₄-alkoxy, C₁-C₄-alkylamino, di-(C₁-C₄-alkyl)amino, C₁-C₄-alkylthioor represents phenyl, phenoxy or phenylthio, each of which is optionallymonosubstituted by fluorine, chlorine, bromine, nitro, cyano,C₁-C₂-alkoxy, trifluoromethoxy or C₁-C₃-alkyl,

[0223] R⁵ very particularly preferably represents methyl, ethyl,methoxy, ethoxy, methylthio or ethylthio,

[0224] R⁶ very particularly preferably represents C₁-C₄-alkyl,C₃-C₆-cycloalkyl, C₁-C₄-alkoxy, C₃-C₄-alkenyl, C₁-C₄-alkoxy-C₁-C₄-alkyl,

[0225] R⁷ very particularly preferably represents hydrogen, C₁-C₄-alkylor C₃-C₄-alkenyl, or

[0226] R⁶ and R⁷ together very particularly preferably represent aC₆-alkylene radical in which optionally one methylene group is replacedby oxygen or sulphur,

[0227] W most preferably represents hydrogen, methyl, ethyl, chlorine orbromine,

[0228] X most preferably represents methyl, ethyl, n-propyl,trifluoromethyl or chlorine,

[0229] Y most preferably represents methyl, trifluoromethyl, chlorine,bromine, represents phenyl which is optionally mono- or disubstituted bychlorine and/or methyl,

[0230] Z most preferably represents hydrogen or methyl, with the provisothat W does not represent bromine if Y represents substituted phenyl,

[0231] A most preferably represents methyl, ethyl or a bond,

[0232] B most preferably represents methyl or ethyl or

[0233] A and B and the carbon atom to which they are attached mostpreferably represent cyclopropyl or cyclohexyl, or

[0234] B and Q¹ together most preferably represent C₄-alkanediyl whichis monosubstituted by methyl,

[0235] Q¹ most preferably represents hydrogen, methyl, methoxy, ethoxy,propoxy, hydroxyl or acetyloxy,

[0236] Q² most preferably represents hydrogen or methyl,

[0237] G most preferably represents hydrogen (a) or represents one ofthe groups

[0238] where

[0239] R¹ most preferably represents C₁-C₄-alkyl or represents phenyl orpyridyl, each of which is optionally monosubstituted by chlorine,

[0240] R² most preferably represents C₁-C₄-alkyl.

[0241] The general or preferred radical definitions or explanationslisted above can be combined with one another as desired, i.e. includingcombinations between the respective ranges and preferred ranges. Theyapply both to the end products and, correspondingly, to the precursorsand intermediates.

[0242] Preference according to the invention is given to the compoundsof the formula (I) which contain a combination of the meanings listedabove as being preferred (preferable).

[0243] Particular preference according to the invention is given to thecompounds of the formula (I) which contain a combination of the meaningslisted above as being particularly preferred.

[0244] Very particular preference according to the invention is given tothe compounds of the formula (I) which contain a combination of themeanings listed above as being very particularly preferred.

[0245] Most preference according to the invention is given to thecompounds of the formula (I) which contain a combination of the meaningslisted above as being most preferred.

[0246] Saturated or unsaturated hydrocarbon radicals such as alkyl oralkenyl can in each case be straight-chain or branched as far as this ispossible, including in combination with hetero atoms, such as, forexample, in alkoxy.

[0247] Unless indicated otherwise, optionally substituted radicals canbe mono- or polysubstituted, and in the case of polysubstitution, thesubstituents can be identical or different.

[0248] Using, according to process (A), ethylO-[(2,4-dichloro)-phenylacetyl] 1-hydroxy-methyl-cyclohexane-carboxylateas starting material, the course of the process according to theinvention can be represented by the following reaction scheme:

[0249] Using, according to process (Bγ),3-[(2-chloro-4-bromo-6-methyl)-phenyl]-5,5,6,6-tetramethyl-5,6-dihydropyroneand 4-chlorophenylboronic acid as starting materials, the course of thereaction can be represented by the following scheme:

[0250] Using, according to process (Cα),3-[(2,4-dichloro)-phenyl]-5,5,6,6-tetramethyl-5,6-dihydropyrone andpivaloyl chloride as starting materials, the course of the processaccording to the invention can be represented by the following reactionscheme:

[0251] Using, according to process (Cβ),3-[(4-bromo-2-chloro-6-ethyl)-phenyl]-6,6-dimethyl-5,6-dihydropyrone andacetic anhydride as starting materials, the course of the processaccording to the invention can be represented by the following reactionscheme:

[0252] Using, according to process (D),3-[(2-chloro-6-ethyl4-phenyl)-phenyl]-5,5-dimethyl-5,6-dihydropyrone andethoxyethyl chloroformate as starting materials, the course of theprocess according to the invention can be represented by the followingreaction scheme:

[0253] Using, according to process (E),3-[2,4,6-trichloro-phenyl]-5,5,6,6-tetramethyl-5,6-dihydropyrone andmethyl chloromonothioformate as starting materials, the course of thereaction can be represented as follows:

[0254] Using, according to process (F),3-(4-chloro-2-methyl-phenyl)-5,5-dimethyl-6-methoxy-5,6-dihydropyroneand methanesulphonyl chloride as starting materials, the course of thereaction can be represented by the following reaction scheme:

[0255] Using, according to process (G),2-(2-methyl-5-bromo-phenyl)-5,5,6,6-tetramethyl-5,6-dihydropyrone and2,2,2-trifluoroethyl methanethio-phosphonate as starting materials, thecourse of the reaction can be represented by the following reactionscheme:

[0256] Using, according to process (H),3-(2,4-dichloro-phenyl)-5,5-pentamethylene-6-methoxy-5,6-dihydropyroneand NaOH as components, the course of the process according to theinvention can be represented by the following reaction scheme:

[0257] Using, according to process (Iα),3-(2,4-dichloro-phenyl)-5,5,6,6-tetramethyl-5,6-dihydropyrone and ethylisocyanate as starting materials, the course of the reaction can berepresented by the following reaction scheme:

[0258] Using, according to process (I),3-(2-chloro-4-bromo-phenyl)-5,5-dimethyl-6-methoxy-5,6-dihydropyrone anddimethylcarbamoyl chloride as starting materials, the course of thereaction can be represented by the following scheme:

[0259] Using chlorocarbonyl 2-mesitylene ketene andtrimethyl-silyloxymethylidene-cyclohexane as starting materials, thecourse of the process (J) according to the invention can be representedby the following formula scheme:

[0260] The compounds of the formula (I)

[0261] in which

[0262] A, B, Q¹, Q², W X, Y, Z and R⁸ are each as defined above,

[0263] required as starting materials in the process (A) according tothe invention are novel.

[0264] The acylhydroxycarboxylic esters of the formula (II) areobtained, for example, when hydroxycarboxylic esters of the formula(XVIII)

[0265] in which

[0266] A, B, Q¹, Q² and R⁸ are each as defined above,

[0267] are acylated with substituted phenylacetyl halides of the formula(XIX)

[0268] in which

[0269] W, X, Y and Z are each as defined above and

[0270] Hal represents chlorine or bromine,

[0271] (see Preparation Examples for compounds of the formula (II)).

[0272] Some of the compounds of the formula (XVIII) are known, or theycan be prepared by processes known in principle, for example byReformatskij synthesis (Organikum, VEB Deutscher Verlag derWissenschaften, Berlin 1990, 18^(th) edition, p. 501 ff.).

[0273] Some of the compounds of the formula (XIX) are known andcommercially available. They can be prepared by processes known inprinciple (see, for example, H. Henecka, Houben-Weyl, Methoden derOrganischen Chemie [Methods of Organic Chemistry], Vol. 8, pp. 467-469(1952), WO 97/02243, WO 99/43649).

[0274] The compounds of the formula (XIX) are obtained, for example, byreacting substituted phenylacetic acids of the formula (XX)

[0275] in which

[0276] W, X, Y and Z are each as defined above,

[0277] with halogenating agents (for example thionyl chloride, thionylbromide, oxalyl chloride, phosgene, phosphorus trichloride, phosphorustribromide or phosphorus pentachloride), if appropriate in the presenceof a diluent (for example optionally chlorinated aliphatic or aromatichydrocarbons, such as toluene or methylene chloride), at temperatures offrom −20° C. to 150° C., preferably from −10° C. to 100° C.

[0278] Some of the compounds of the formula (XX) are commerciallyavailable, some are known, or they can be prepared by processes known inprinciple (for example WO 97/02243, WO 99/43649).

[0279] Some of the silylacetylenes of the formula (III) required forcarrying out the process B(α) are commercially available, or they can beprepared by generally known processes. Some of the vinylstannanes of theformula (IV) required for carrying out the process B(β) are likewisecommercially available, or they can be prepared by known processes.

[0280] Some of the boronic acids of the formula (V)

[0281] in which

[0282] Y represents optionally substituted phenyl or hetaryl,

[0283] required for carrying out the process B(y) are commerciallyavailable, or they can be prepared in a simple manner by generally knownprocesses.

[0284] The formula (XVI) provides a general definition of the silyl enolethers required as starting materials for carrying out the process (J)according to the invention. In this formula, A and B each preferablyhave those meanings which have already been mentioned in connection withthe description of the 5,6-dihydro-pyrones of the formula (I) accordingto the invention as being preferred for these radicals. Alk preferablyrepresents methyl or ethyl, particularly preferably methyl.

[0285] The silyl enol ethers of the formula (XVI) are known or can beprepared by known methods.

[0286] The formula (XIV) provides a general definition of the ketenederivatives required as reaction components for carrying out the processaccording to the invention. In this formula, W, X, Y and Z eachpreferably have those meanings which have already been mentioned inconnection with the description of the 5,6-dihydro-pyrones of theformula (I) according to the invention as being preferred for theseradicals. Hal also preferably represents chlorine or bromine.

[0287] Ketene derivatives of the formula (XVII) are known or can beprepared by known processes (cf. Org. Prep. Proced. Int. 7, 155-158(1975) and DE-A 1 945 703). Thus, ketene derivatives of the formula(XVII) are obtained by reacting substituted phenylmalonic acids of theformula (XXI)

[0288] in which

[0289] W, X, Y and Z are each as defined above,

[0290] with acid halides, such as, for example, thionyl chloride,phosphorus(V) chloride, phosphorus(III) chloride, oxalyl chloride,phosgene or thionyl bromide, if appropriate in the presence ofcatalysts, such as, for example, diethylformamide,methyl-stearyl-formamide or triphenylphosphine and if appropriate in thepresence of bases such as, for example, pyridine or triethylamine, at atemperature between −20° C. and +200° C., preferably between 0° C. and150° C.

[0291] The substituted phenylmalonic acids of the formula (XXI) areknown or can be prepared by known methods (cf., for example, Organikum,VEB Deutscher Verlag der Wissenschaften, Berlin 1977, p. 517 ff.). Thus,substituted phenylmalonic acids of the formula (XXI) are obtained byreacting substituted phenylmalonic esters of the formula

[0292] in which

[0293] W, X, Y and Z are each as defined above and

[0294] R⁹ represents alkyl having 1 to 4 carbon atoms,

[0295] with alkali metal hydroxides, such as sodium hydroxide orpotassium hydroxide, in the presence of a diluent, such as water, attemperatures between 0° C. and 30° C.

[0296] In the formula (XXII), W, X, Y and Z each preferably have thosemeanings which have already been mentioned in connection with thedescription of the 5,6-dihydro-pyrones of the formula (I) according tothe invention as being preferred for these radicals. R⁹ preferablyrepresents methyl or ethyl.

[0297] The substituted phenylmalonic esters of the formula (XXII) areknown or can be prepared by known methods (cf. Tetrahedron Letters 27,2763 (1986) and Organikum, VEB Deutscher Verlag der Wissenschaften,Berlin 1977, p.587 ff.).

[0298] The acyl halides of the formula (VI), carboxylic anhydrides ofthe formula (VII), chloroformic esters or chloroformic thioesters of theformula (VIII), chloromonothioformic esters or chlorodithioformic estersof the formula (IX), sulphonyl chlorides of the formula (X), phosphoruscompounds of the formula (XI) and metal hydroxides, metal alkoxides oramines of the formulae (XII) and (XIII) and isocyanates of the formula(XIV) and carbamoyl chlorides of the formula (XV) furthermore requiredas starting materials for carrying out the processes (C), (D), (E), (F),(G), (H) and (I) according to the invention are generally knowncompounds of organic or inorganic chemistry.

[0299] The process (A) is characterized in that compounds of the formula(II) in which A, B, Q¹, Q², W, X, Y, Z and R⁸ are each as defined aboveare subjected to an intramolecular condensation in the presence of abase.

[0300] Suitable diluents for use in the process (A) according to theinvention are all inert organic solvents. Preference is given to usinghydrocarbons, such as toluene and xylene, furthermore ethers, such asdibutyl ether, tetrahydrofuran, dioxane, glycol dimethyl ether anddiglycol dimethyl ether, moreover polar solvents, such as dimethylsulphoxide, sulpholane, dimethylformamide and N-methylpyrrolidone, andalso alcohols, such as methanol, ethanol, propanol, iso-propanol,butanol, iso-butanol and tert-butanol.

[0301] Suitable bases (deprotonating agents) for carrying out theprocess (A) according to the invention are all customary protonacceptors. Preference is given to using alkali metals and alkaline earthmetal oxides, hydroxides and carbonates, such as sodium hydroxide,potassium hydroxide, magnesium, oxide, calcium oxide, sodium carbonate,potassium carbonate and calcium carbonate, which can also be used in thepresence of phase-transfer catalysts, such as, for example,triethylbenzylammonium chloride, tetrabutylammonium bromide, Adogen 464(=methyltrialkyl(C₈-C₁₀)ammonium chloride) or TDA 1(=tris-(methoxyethoxyethyl)-amine). It is furthermore possible to usealkali metals such as sodium or potassium. Also suitable are alkalimetal and alkaline earth metal amides and hydrides, such as sodiumamide, sodium hydride and calcium hydride, and furthermore also alkalimetal alkoxides, such as sodium methoxide, sodium ethoxide and potassiumtert-butoxide.

[0302] When carrying out the process (A) according to the invention, thereaction temperatures can be varied within a relatively wide range. Ingeneral, the process is carried out at temperatures between 0° C. and250° C., preferably between 50° C. and 150° C.

[0303] The process (A) according to the invention is generally carriedout under atmospheric pressure.

[0304] When carrying out the process (A) according to the invention, thereaction components of the formula (II) and the deprotonating bases aregenerally employed in about double equimolar amounts. However, it isalso possible to use a relatively large excess (up to 3 mol) of onecomponent or the other.

[0305] Suitable catalysts for carrying out the processes B (α) to B (γ)according to the invention are palladium(0) complexes. Use is made, forexample, of tetrakis(tri-phenylphosphine)palladium. Also suitable arepalladium(II) compounds, such as bis(triphenylphosphine)palladium(II)chloride.

[0306] Suitable acid acceptors for carrying out the processes B (α) andB (γ) according to the invention are inorganic or organic bases. Thesepreferably include alkaline earth metal or alkali metal hydroxides,acetates, carbonates or bicarbonates, such as, for example, sodiumhydroxide, potassium hydroxide, barium hydroxide or ammonium hydroxide,sodium acetate, potassium acetate, calcium acetate or ammonium acetate,sodium carbonate, potassium carbonate or ammonium carbonate, sodiumbicarbonate or potassium bicarbonate, alkali metal fluorides, such as,for example, potassium fluoride or caesium fluoride, and also tertiaryamines, such as trimethylamine, triethylamine, tributylamine,N,N-dimethylaniline, N,N-dimethylbenzylamine, pyridine,N-methylpiperidine, N-methylmorpholine, N,N-dimethylaminopyridine,diazabicyclooctane (DABCO), diazabicyclononene (DBN) ordiazabicycloundecene (DBU).

[0307] Suitable diluents for carrying out the process B (γ) according tothe invention are water, organic solvents and any mixtures thereof.Examples of organic solvents suitable for processes B (α) to B (γ) are:aliphatic, alicyclic or aromatic hydrocarbons, such as, for example,petroleum ether, hexane, heptane, cyclohexane, methylcyclohexane,benzene, toluene, xylene or decalin; halogenated hydrocarbons, such as,for example, chlorobenzene, dichlorobenzene, methylene chloride,chloroform, carbon tetrachloride, dichloroethane, trichloroethane ortetra-chloroethylene; ethers, such as diethyl ether, diisopropyl ether,methyl tert-butyl ether, methyl tert-amyl ether, dioxane,tetrahydrofuran, 1,2-dimethoxyethane, 1,2-diethoxyethane, diethyleneglycol dimethyl ether or anisole; alcohols, such as methanol, ethanol,n- or iso-propanol, n-, iso-, sec- or tert-butanol, ethanediol,propane-1,2-diol, ethoxyethanol, methoxyethanol, diethylene glycolmonomethyl ether; diethylene glycol monoethyl ether; water.

[0308] The reaction temperature in process (B) according to theinvention can be varied within a relatively wide range. In general, theprocess is carried out at temperatures between 0° C. and +180° C.,preferably between 50° C. and +150° C.

[0309] When carrying out the process B (α), silylacetylenes of theformula (III) and compounds of the formulae (I-a′) to (I-g′) areemployed in a molar ratio of from 1:1 to 10:1, preferably from 1:1 to3:1. When carrying out the process B(β), vinylstannanes of the formula(IV) and compounds of the formulae (I-a′) to (I-g′) are employed in amolar ratio of from 1:1 to 10:1, preferably from 1:1 to 3:1.

[0310] When carrying out the process B (γ) according to the invention,boronic acids of the formula (V) and compounds of the formulae (I-a′)and (I-g′) are employed in a molar ratio of from 1:1 to 3:1, preferablyfrom 1:1 to 2:1.

[0311] The catalyst is generally employed in amounts of from 0.005 to0.5 mol, preferably from 0.01 to 0.1 mol, per mole of the compounds(I-a′) to (I-g′). The base is generally employed in excess.

[0312] The process (C-α) is characterized in that compounds of theformula (I-a) are in each case reacted with carbonyl halides of theformula (VI), if appropriate in the presence of a diluent and ifappropriate in the presence of an acid binder.

[0313] Suitable diluents for use in the process (C-α) according to theinvention are all solvents which are inert to the acyl halides.Preference is given to using hydrocarbons, such as benzene, benzene,toluene, xylene and tetralin, furthermore halogenated hydrocarbons, suchas methylene chloride, chloroform, carbon tetrachloride, chlorobenzeneand o-dichlorobenzene, moreover ketones, such as acetone and methylisopropyl ketone, furthermore ethers, such as diethyl ether,tetra-hydrofuran and dioxane, additionally carboxylic esters, such asethyl acetate, nitriles, such as acetonitrile, and also strongly polarsolvents, such as dimethylformamide, dimethyl sulphoxide and sulpholane.The hydrolytic stability of the acyl halide permitting, the reaction canalso be carried out in the presence of water.

[0314] Suitable acid binders for the reaction according to the process(C-α) according to the invention are all customary acid acceptors.Preference is given to using tertiary amines, such as triethylamine,pyridine, diazabicyclooctane (DABCO), diazabi-cycloundecene (DBU),diazabicyclononene (DBN), Hünig base and N,N-dimethyl-aniline,furthermore alkaline earth metal oxides, such as magnesium oxide andcalcium oxide, moreover alkali metal carbonates and alkaline earth metalcarbonates, such as sodium carbonate, potassium carbonate and calciumcarbonate, and also alkali metal hydroxides, such as sodium hydroxideand potassium hydroxide.

[0315] The reaction temperatures in the process (C-α) according to theinvention can be varied within a relatively wide range. In general, theprocess is carried out at temperatures between −20° C. and +150° C.,preferably between 0° C. and 100° C.

[0316] When carrying out the process (C-α) according to the invention,the starting materials of the formula (I-a) and the carbonyl halide ofthe formula (VI) are generally each employed in approximately equivalentamounts. However, it is also possible to use a relatively large excess(up to 5 mol) of carbonyl halide. Work-up is carried out by customarymethods.

[0317] The process (C-β) is characterized in that compounds of theformula (I-a) are reacted with carboxylic anhydrides of the formula(VII), if appropriate in the presence of a diluent and if appropriate inthe presence of an acid binder.

[0318] Suitable diluents for use in the process (C-β) according to theinvention are preferably those diluents which are also preferred whenusing acyl halides. Furthermore, it is also possible for excesscarboxylic anhydride to act simultaneously as diluent.

[0319] Suitable acid binders for process (C-β), which are added, ifappropriate, are preferably those acid binders which are also preferredwhen using acyl halides.

[0320] The reaction temperatures in the process (C-β) according to theinvention can be varied within a relatively wide range. In general, theprocess is carried out at temperatures between −20° C. and +150° C.,preferably between 0° C. and 100° C.

[0321] When carrying out the process (C-β) according to the invention,the starting materials of the formula (I-a) and the carboxylic anhydrideof the formula (VII) are generally each employed in approximatelyequivalent amounts. However, it is also possible to use a relativelylarge excess (up to 5 mol) of carboxylic anhydride. Work-up is carriedout by customary methods.

[0322] In general, diluent and excess carboxylic anhydride and thecarboxylic acid formed are removed by distillation or by washing with anorganic solvent or with water.

[0323] The process (D) is characterized in that compounds of the formula(I-a) are in each case reacted with chloroformic esters or chloroformicthioesters of the formula (VIII), if appropriate in the presence of adiluent and if appropriate in the presence of an acid binder.

[0324] Acid binders suitable for the reaction according to process (D)according to the invention are all customary acid acceptors. Preferenceis given to using tertiary amines, such as triethylamine, pyridine,DABCO, DBU, DBA, Hünig base and N,N-dimethyl-aniline, furthermorealkaline earth metal oxides, such as magnesium oxide and calcium oxide,moreover alkali metal and alkaline earth metal carbonates, such assodium carbonate, potassium carbonate and calcium carbonate, and alsoalkali metal hydroxides, such as sodium hydroxide and potassiumhydroxide.

[0325] Suitable diluents for use in the process (D) according to theinvention are all solvents which are inert to the chloroformic esters orchloroformic thioesters. Preference is given to using hydrocarbons, suchas benzene, benzene, toluene, xylene and tetralin, furthermorehalogenated hydrocarbons, such as methylene chloride, chloroform, carbontetrachloride, chlorobenzene and o-dichlorobenzene, moreover ketones,such as acetone and methyl isopropyl ketone, furthermore ethers, such asdiethyl ether, tetrahydrofuran and dioxane, additionally carboxylicesters, such as ethyl acetate, nitriles, such as acetonitrile, and alsostrongly polar solvents, such as dimethylformamide, dimethyl sulphoxideand sulpholane.

[0326] When carrying out the process (D) according to the invention, thereaction temperatures can be varied within a relatively wide range. Ifthe reaction is carried out in the presence of a diluent and an acidbinder, the reaction temperatures are generally between −20° C. and+100° C., preferably between 0° C. and 50° C.

[0327] The process (D) according to the invention is generally carriedout under atmospheric pressure.

[0328] When carrying out the process (D) according to the invention, thestarting materials of the formula (I-a) and the appropriate chloroformicester or chloroformic thioester of the formula (VIII) are generally eachemployed in approximately equivalent amounts. However, it is alsopossible to use a relatively large excess (up to 2 mol) of one componentor the other. Work-up is carried out by customary methods. In general,precipitated salts are removed, and the reaction mixture that remains isconcentrated by removing the diluent under reduced pressure.

[0329] The process (E) according to the invention is characterized inthat compounds of the formula (I-a) are in each case reacted withcompounds of the formula (IX) in the presence of a diluent and, ifappropriate, in the presence of an acid binder.

[0330] In preparation process (E), about 1 mol of chloromonothioformicester or chlorodithioformic ester of the formula (IX) are employed permole of starting material of the formula (I-a), at from 0 to 120° C.,preferably from 20 to 60° C.

[0331] Suitable diluents, which are added, if appropriate, are all inertpolar organic solvents, such as nitrites, ethers, esters, amides,sulphones, sulphoxides, but also halogenoalkanes.

[0332] Preference is giving to using acetonitrile, ethyl acetate,dimethyl sulphoxide, tetrahydrofuran, dimethylformamide or methylenechloride.

[0333] If, in a preferred embodiment, the enolate salt of the compound(I-a) is prepared by addition of strong deprotonating agents, such as,for example, sodium hydride or potassium tert-butoxide, the furtheraddition of acid binders can be dispensed with.

[0334] If acid binders are used, these can be customary inorganic ororganic bases, examples that may be mentioned being sodium hydroxide,sodium carbonate, potassium carbonate, pyridine and triethylamine.

[0335] The reaction can be carried out at atmospheric pressure or underelevated pressure and is preferably carried out at atmospheric pressure.Work-up is carried out by customary methods.

[0336] The process (F) according to the invention is characterized inthat compounds of the formula (I-a) are in each case reacted withsulphonyl chlorides of the formula (X), if appropriate in the presenceof a diluent and if appropriate in the presence of an acid binder.

[0337] In preparation process (F), about 1 mol of sulphonyl chloride ofthe formula (X) is used per mole of starting material of the formula, atfrom −20 to 150° C., preferably from 20 to 70° C.

[0338] Suitable diluents, which are added, if appropriate, are all inertpolar organic solvents, such as esters, ethers, amides, nitrites,sulphones, sulphoxides, or halogenated hydrocarbons, such as methylenechloride.

[0339] Preference is given to using acetonitrile, ethyl acetate,dimethyl sulphoxide, tetrahydrofuran, dimethylformamide of methylenechloride.

[0340] If, in a preferred embodiment, the enolate salt of the compound(I-a) is prepared by addition of strong deprotonating agents (such as,for example, sodium hydride or potassium tert-butoxide), the furtheraddition of acid binders can be dispensed with.

[0341] If acid binders are used, these can be customary inorganic ororganic bases, examples which may be mentioned being sodium hydroxide,sodium carbonate, potassium carbonate, pyridine and triethylamine.

[0342] The reaction can be carried out at atmospheric pressure or underelevated pressure and is preferably carried out at atmospheric pressure.Work-up is carried out by customary methods.

[0343] The process (G) according to the invention is characterized inthat compounds of the formula (I-a) are in each case reacted withphosphorus compounds of the formula (XI), if appropriate in the presenceof a diluent and if appropriate in the presence of an acid binder.

[0344] In preparation process (G), from 1 to 2, preferably from 1 to1.3, mol of the phosphorus compound of the formula (XI) are used permole of the compound (I-a), at temperatures between −40° C. and 150° C.,preferably between −10 and 110° C., to give compounds of the formula(I-e).

[0345] Suitable diluents which may be added, if appropriate, are allinert polar organic solvents, such as ethers, amides, nitriles,alcohols, sulphides, sulphones, sulphoxides. etc.

[0346] Preference is given of using acetonitrile, dimethyl sulphoxide,tetrahydrofuran, dimethylformamide or methylene chloride.

[0347] Suitable acid binders, which may be added, if appropriate, arecustomary inorganic or organic bases, such as hydroxides, carbonates oramines. Examples which may be mentioned are sodium hydroxide, sodiumcarbonate, potassium carbonate, pyridine and triethylamine.

[0348] The reaction can be carried out at atmospheric pressure or underelevated pressure and is preferably carried out at atmospheric pressure.Work-up is carried out by customary methods of organic chemistry. Thepurification of the resulting end product is preferably carried out bycrystallization, chromatographic purification or by so-called “incipientdistillation”, i.e. removal of the volatile components under reducedpressure.

[0349] The process (H) is characterized in that compounds of the formula(I-a) are reacted with metal hydroxides or metal alkoxides of theformula (XII) or amines of the formula (XIII), if appropriate in thepresence of a diluent.

[0350] Preferred diluents for the process (H) according to the inventionare ethers, such as tetrahydrofuran, dioxane or diethyl ether, or elsealcohols, such as methanol, ethanol, isopropanol, but also water.

[0351] The process (H) according to the invention is generally carriedout under atmospheric pressure.

[0352] The reaction temperatures are generally between −20° C. and 100°C., preferably between 0° C. and 50° C.

[0353] The process (I) according to the invention is characterized inthat (I-α) compounds of the formula (I-a) are in each case reacted withcompounds of the formula (XIV), if appropriate in the presence of adiluent and if appropriate in the presence of a catalyst, or (I-β) withcompounds of the formula (XV), if appropriate in the presence of adiluent and if appropriate in the presence of an acid binder.

[0354] In preparation process (I-α), about 1 mol of isocyanate of theformula (XIV) is used per mole of starting material of the formula(I-a), at from 0 to 100° C., preferably at from 20 to 50° C.

[0355] Suitable diluents which are added, if appropriate, are all inertorganic solvents, such as nitrites, esters, ethers, amides, sulphonesand sulphoxides.

[0356] If appropriate, catalysts may be added to accelerate thereaction. Particularly advantageous catalysts are organotin compounds,such as, for example, dibutyltin dilaurate. The process is preferablycarried out at atmospheric pressure.

[0357] In preparation process (I-β), about I mol of carbamoyl chlorideof the formula (XV) is used per mole of starting material of the formula(I-a), at from −20 to 150° C., preferably at from 0 to 70° C.

[0358] Suitable diluents which are added, if appropriate, are all inertpolar organic solvents, such as nitrites, esters, ethers, amides,sulphones, sulphoxides, or halogenated hydrocarbons.

[0359] Preference is given to using acetonitrile, ethyl acetate,dimethyl sulphoxide, tetrahydrofuran, dimethylformamide or methylenechloride.

[0360] If, in a preferred embodiment, the enolate salt of the compound(I-a) is prepared by addition of strong deprotonating agents (such as,for example, sodium hydride or potassium tert-butoxide), the furtheraddition of acid binders can be dispensed with.

[0361] If acid binders are used, these can be customary inorganic ororganic bases, examples which may be mentioned being sodium hydroxide,sodium carbonate, potassium carbonate, triethylamine and pyridine.

[0362] The reaction can be carried out at atmospheric pressure or underelevated pressure and is preferably carried out at atmospheric pressure.Work-up is carried out by customary methods.

[0363] Suitable diluents for carrying out the process (J) according tothe invention are all customary organic solvents which are inert towardsthe reactants. Preference is given to using hydrocarbons, such aso-dichlorobenzene, tetralin, toluene and xylene, furthermore ethers,such as dibutyl ether, glycol dimethyl ether and diglycol dimethylether, moreover polar solvents, such as dimethyl sulphoxide, sulpholane,dimethylformamide or N-methylpyrrolidone. Suitable cosolvents accordingto Example (I-2-a) are alcohols, such as methanol, ethanol, propanol orbutanol, but also water.

[0364] Suitable acid acceptors for carrying out the process (J)according to the invention are all customary acid binders. Preference isgiving to using tertiary amines, such as triethylamine, pyridine,diazabicyclooctane (DABCO), diazabicycloundecene (DBU),diazabicyclononene (DBN), Hünig base or N,N-dimethylaniline.

[0365] When carrying out the process (J) according to the invention, thereaction temperatures can be varied within a relatively wide range. Theprocess is expediently carried out at temperatures between 0° C. and250° C., preferably between 50° C. and 220° C.

[0366] The process (J) according to the invention is preferably carriedout under atmospheric pressure.

[0367] When carrying out the process (J) according to the invention, ingeneral an equimolar amount of the ketene derivative of the formula(XVII) and if appropriate also an equimolar amount of acid acceptor areused per mole of silyl ether of the formula (XVI). However, it is alsopossible to use a relatively large excess (up to 5 mol) of one componentor the other.

[0368] The 5,6-dihydro-pyrones of the formula (I) according to theinvention have very good pesticidal activity and are highly compatiblewith crop plants.

[0369] The active compounds are suitable for controlling animal pests,in particular insects, arachnids and nematodes found in agriculture, inforests, in the protection of stored products and materials and in thehygiene sector, and they are tolerated well by plants and havefavourable homeotherm toxicity. They are preferably employed as cropprotection agents. They are active against normally sensitive andresistant species, and against all or individual developmental stages.The abovementioned pests include:

[0370] From the order of the Isopoda, for example, Oniscus asellus,Armadillidium vulgare, Porcellio scaber.

[0371] From the order of the Diplopoda, for example, Blaniulusguttulatus.

[0372] From the order of the Chilopoda, for example, Geophiluscarpophagus, Scutigera spp.

[0373] From the order of the Symphyla, for example, Scutigerellaimmaculata.

[0374] From the order of the Thysanura, for example, Lepisma saccharina.

[0375] From the order of the Collembola, for example, Onychiurusarmatus.

[0376] From the order of the Orthoptera, for example, Acheta domesticus,Gryllotalpa spp., Locusta migratoria migratorioides, Melanoplus spp.,Schistocerca gregaria.

[0377] From the order of the Blattaria, for example, Blatta orientalis,Periplaneta americana, Leucophaea maderae, Blattella germanica.

[0378] From the order of the Dermaptera, for example, Forficulaauricularia.

[0379] From the order of the Isoptera, for example, Reticulitermes spp.

[0380] From the order of the Phthiraptera, for example, Pediculushumanus corporis, Haematopinus spp., Linognathus spp., Trichodectesspp., Damalinia spp.

[0381] From the order of the Thysanoptera, for example, Hercinothripsfemoralis, Thrips tabaci, Thrips palmi, Frankliniella occidentalis.

[0382] From the order of the Heteroptera, for example, Eurygaster spp.,Dysdercus intermedius, Piesma quadrata, Cimex lectularius, Rhodniusprolixus, Triatoma spp.

[0383] From the order of the Homoptera, for example, Aleurodesbrassicae, Bemisia tabaci, Trialeurodes vaporariorum, Aphis gossypii,Brevicoryne brassicae, Cryptomyzus ribis, Aphis fabae, Aphis pomi,Eriosoma lanigerum, Hyalopterus arundinis, Phylloxera vastatrix,Pemphigus spp., Macrosiphum avenae, Myzus spp., Phorodon humuli,Rhopalosiphum padi, Empoasca spp., Euscelis bilobatus, Nephotettixcincticeps, Lecanium comi, Saissetia oleae, Laodelphax striatellus,Nilaparvata lugens, Aonidiella aurantii, Aspidiotus hederae,Pseudococcus spp., Psylla spp.

[0384] From the order of the Lepidoptera, for example, Pectinophoragossypiella, Bupalus piniarius, Cheimatobia brumata, Lithocolletisblancardella, Hyponomeuta padella, PlutelIa xylostella, Malacosomaneustria, Euproctis chrysorrhoea, Lymantria spp., Bucculatrixthurberiella, Phyllocnistis citrella, Agrotis spp., Euxoa spp., Feltiaspp., Earias insulana, Heliothis spp., Mamestra brassicae, Panolisflammea, Spodoptera spp., Trichoplusia ni, Carpocapsa pomonella, Pierisspp., Chilo spp., Pyrausta nubilalis, Ephestia kuehniella, Galleriamellonella, Tineola bisselliella, Tinea pellionella, Hofmannophilapseudospretella, Cacoecia podana, Capua reticulana, Choristoneurafumiferana, Clysia ambiguella, Homona magnanima, Tortrix viridana,Cnaphalocerus spp., Oulema oryzae.

[0385] From the order of the Coleoptera, for example, Anobium punctatum,Rhizopertha dominica, Bruchidius obtectus, Acanthoscelides obtectus,Hylotrupes bajulus, Agelastica alni, Leptinotarsa decemlineata, Phaedoncochleariae, Diabrotica spp., Psylliodes chrysocephala, Epilachnavarivestis, Atomaria spp., Oryzaephilus surinamensis, Anthonomus spp.,Sitophilus spp., Otiorrhynchus sulcatus, Cosmopolites sordidus,Ceuthorrhynchus assimilis, Hypera postica, Dermestes spp., Trogodermaspp., Anthrenus spp., Attagenus spp., Lyctus spp., Meligethes aeneus,Ptinus spp., Niptus hololeucus, Gibbium psylloides, Tribolium spp.,Tenebrio molitor, Agriotes spp., Conoderus spp., Melolontha melolontha,Amphimallon solstitialis, Costelytra zealandica, Lissorhoptrusoryzophilus.

[0386] From the order of the Hymenoptera, for example, Diprion spp.,Hoplocampa spp., Lasius spp., Monomorium pharaonis, Vespa spp.

[0387] From the order of the Diptera, for example, Aedes spp., Anophelesspp., Culex spp., Drosophila melanogaster, Musca spp., Fannia spp.,Calliphora erythrocephala, Lucilia spp., Chrysomyia spp., Cuterebraspp., Gastrophilus spp., Hyppobosca spp., Stomoxys spp., Oestrus spp.,Hypoderma spp., Tabanus spp., Tannia spp., Bibio hortulanus, Oscinellafrit, Phorbia spp., Pegomyia hyoscyami, Ceratitis capitata, Dacus oleae,Tipula paludosa, Hylemyia spp., Liriomyza spp.

[0388] From the order of the Siphonaptera, for example, Xenopsyllacheopis, Ceratophyllus spp.

[0389] From the class of the Arachnida, for example, Scorpio maurus,Latrodectus mactans, Acarus siro, Argas spp., Ornithodoros spp.,Dermanyssus gallinae, Eriophyes ribis, Phyllocoptruta oleivora,Boophilus spp., Rhipicephalus spp., Amblyomma spp., Hyalomma spp.,Ixodes spp., Psoroptes spp., Chorioptes spp., Sarcoptes spp., Tarsonemusspp., Bryobia praetiosa, Panonychus spp., Tetranychus spp.,Hemitarsonemus spp., Brevipalpus spp.

[0390] The plant-parasitic nematodes include, for example, Pratylenchusspp., Radopholus similis, Ditylenchus dipsaci, Tylenchulussemipenetrans, Heterodera spp., Globodera spp., Meloidogyne spp.,Aphelenchoides spp., Longidorus spp., Xiphinema spp., Trichodorus spp.,Bursaphelenchus spp.

[0391] At certain concentrations or application rates, the compoundsaccording to the invention can, if appropriate, also be employed asherbicides and microbicides, for example as fungicides, antimycotics andbactericides. If appropriate, they can also be used as intermediates orprecursors for the synthesis of further active compounds.

[0392] The active compounds can be converted into the customaryformulations such as solutions, emulsions, wettable powders,suspensions, powders, dusts, pastes, soluble powders, granules,suspension-emulsion concentrates, natural and synthetic materialsimpregnated with active compound, and microencapsulations in polymericmaterials.

[0393] These formulations are produced in a known manner, for example bymixing the active compounds with extenders, that is, liquid solventsand/or solid carriers, optionally with the use of surfactants, that is,emulsifiers and/or dispersants, and/or foam formers.

[0394] If the extender used is water, it is also possible, for example,to use organic solvents as cosolvents. The following are essentiallysuitable as liquid solvents: aromatics such as xylene, toluene oralkylnaphthalenes, chlorinated aromatics or chlorinated aliphatichydrocarbons such as chlorobenzenes, chloroethylenes or methylenechloride, aliphatic hydrocarbons such as cyclohexane or paraffins, forexample mineral oil fractions, mineral and vegetable oils, alcohols suchas butanol or glycol and their ethers and esters, ketones such asacetone, methyl ethyl ketone, methyl isobutyl ketone or cyclohexanone,strongly polar solvents such as dimethylformamide and dimethylsulphoxide, or else water.

[0395] Suitable solid carriers are:

[0396] for example ammonium salts and ground natural minerals such askaolins, clays, talc, chalk, quartz, attapulgite, montmorillonite ordiatomaceous earth, and ground synthetic materials such ashighly-disperse silica, alumina and silicates; suitable solid carriersfor granules are: for example crushed and fractionated natural rockssuch as calcite, marble, pumice, sepiolite and dolomite, or elsesynthetic granules of inorganic and organic meals, and granules oforganic material such as sawdust, coconut shells, maize cobs and tobaccostalks; suitable emulsifiers and/or foam formers are: for examplenonionic and anionic emulsifiers such as polyoxyethylene 5 fatty acidesters, polyoxyethylene fatty alcohol ethers, for example alkylarylpolyglycol ethers, alkylsulphonates, alkyl sulphates, arylsulphonates,or else protein hydrolysates; suitable dispersants are: for examplelignin-sulphite waste liquors and methylcellulose.

[0397] Tackifiers such as carboxymethylcellulose and natural andsynthetic polymers in the form of powders, granules or latices, such asgum arabic, polyvinyl alcohol and polyvinyl acetate, or else naturalphospholipids such as cephalins and lecithins and syntheticphospholipids can be used in the formulations. Other additives can bemineral and vegetable oils.

[0398] It is possible to use colorants such as inorganic pigments, forexample iron oxide, titanium oxide and Prussian Blue, and organiccolorants such as alizarin colorants, azo colorants and metalphthalocyanine colorants, and trace nutrients such as salts of iron,manganese, boron, copper, cobalt, molybdenum and zinc.

[0399] The formulations generally comprise between 0.1 and 95% by weightof active compound, preferably between 0.5 and 90%.

[0400] The active compound according to the invention can be present inits commercially available formulations and in the use forms, preparedfrom these formulations, as a mixture with other active compounds, suchas insecticides, attractants, sterilants, bactericides, acaricides,nematicides, fungicides, growth-regulating substances or herbicides. Theinsecticides include, for example, phosphates, carbamates, carboxylates,chlorinated hydrocarbons, phenylureas and substances produced bymicroorganisms.

[0401] Examples of particularly advantageous mixing components are thefollowing:

[0402] Fungicides

[0403] aldimorph, ampropylfos, ampropylfos potassium, andoprim,anilazine, azaconazole, azoxystrobin,

[0404] benalaxyl, benodanil, benomyl, benzamacril, benzamacril-isobutyl,bialaphos, binapacryl, biphenyl, bitertanol, blasticidin-S,bromuconazole, bupirimate, buthiobate,

[0405] calcium polysulphide, capsimycin, captafol, captan, carbendazim,carboxin, carvon, quinomethionate, chlobenthiazone, chlorfenazole,chloroneb, chloropicrin, chlorothalonil, chlozolinate, clozylacon,cufraneb, cymoxanil, cyproconazole, cyprodinil, cyprofuram,

[0406] debacarb, dichlorophen, diclobutrazole, diclofluanid,diclomezine, dicloran, diethofencarb, difenoconazole, dimethirimol,dimethomorph, diniconazole, diniconazole-M, dinocap, diphenylamine,dipyrithione, ditalimfos, dithianon, dodemorph, dodine, drazoxolon,

[0407] edifenphos, epoxiconazole, etaconazole, ethirimol, etridiazole,

[0408] famoxadon, fenapanil, fenarimol, fenbuconazole, fenfuram,fenitropan, fenpiclonil, fenpropidin, fenpropimorph, fentin acetate,fentin hydroxide, ferbam, ferimzone, fluazinam, flumetover, fluoromide,fluquinconazole, flurprimidol, flusilazole, flusulfamide, flutolanil,flutriafol, folpet, fosetyl-aluminium, fosetyl-sodium, fthalide,fuberidazole, furalaxyl, furametpyr, furcarbonil, furconazole,furconazole-cis, furmecyclox,

[0409] guazatine,

[0410] hexachlorobenzene, hexaconazole, hymexazole,

[0411] imazalil, imibenconazole, iminoctadine, iminoctadine albesilate,iminoctadine triacetate, iodocarb, ipconazole, iprobenfos (IBP),iprodione, irumamycin, isoprothiolane, isovaledione,

[0412] kasugamycin, kresoxim-methyl, copper preparations, such as:copper hydroxide, copper naphthenate, copper oxychloride, coppersulphate, copper oxide, oxine-copper and Bordeaux mixture,

[0413] mancopper, mancozeb, maneb, meferimzone, mepanipyrim, mepronil,metalaxyl, metconazole, methasulfocarb, methfuroxam, metiram,metomeclam, metsulfovax, mildiomycin, myclobutanil, myclozolin,

[0414] nickel dimethyldithiocarbamate, nitrothal-isopropyl, nuarimol,

[0415] ofurace, oxadixyl, oxamocarb, oxolinic acid, oxycarboxim,oxyfenthiin,

[0416] paclobutrazole, pefurazoate, penconazole, pencycuron, phosdiphen,picoxystrobin, pimaricin, piperalin, polyoxin, polyoxorim, probenazole,prochloraz, procymidone, propamocarb, propanosine-sodium, propiconazole,propineb, pyraclostrobin, pyrazophos, pyrifenox, pyrimethanil,pyroquilon, pyroxyfur,

[0417] quinconazole, quintozene (PCNB),

[0418] sulphur and sulphur preparations,

[0419] tebuconazole, tecloftalam, tecnazene, tetcyclacis, tetraconazole,thiabendazole, thicyofen, thifluzamide, thiophanate-methyl, thiram,tioxymid, tolclofos-methyl, tolylfluanid, triadimefon, triadimenol,triazbutil, triazoxide, trichlamide, tricyclazole, tridemorph,trifloxystrobin, triflumizole, triforine, triticonazole,

[0420] uniconazole,

[0421] validamycin A, vinclozolin, viniconazole,

[0422] zarilamide, zineb, ziram and also

[0423] Dagger G,

[0424] OK-8705,

[0425] OK-8801,

[0426]α-(1,1-dimethylethyl)-β-(2-phenoxyethyl)-1H-1,2,4-triazole-1-ethanol,

[0427]α-(2,4-dichlorophenyl)-β-fluoro-β-propyl-1H-1,2,4-triazole-1-ethanol,

[0428]α-(2,4-dichlorophenyl)-β-methoxy-α-methyl-1H-1,2,4-triazole-1-ethanol,

[0429]α-(5-methyl-1,3-dioxan-5-yl)-β-[[4-(trifluoromethyl)-phenyl]-methylene]-1H-1,2,4-triazole-1-ethanol,

[0430] (5RS,6RS)-6-hydroxy-2,2,7,7-tetramethyl-5-(1H-1,2,4-triazol-1-yl)-3-octanone,(E)-α-(methoxyimino)-N-methyl-2-phenoxy-phenylacetamide,

[0431] 1-isopropyl{2-methyl-1-[[[1-(4-methylphenyl)-ethyl]-amino]-carbonyl]-propyl}-carbamate,

[0432] 1-(2,4-dichlorophenyl)-2-(1H-1,2,4-triazol-1-yl)-ethanoneO-(phenylmethyl)-oxime,

[0433] 1-(2-methyl-1-naphthalenyl)-1H-pyrrole-2,5-dione,

[0434] 1-(3,5-dichlorophenyl)-3-(2-propenyl)-2,5-pyrrolidinedione,

[0435] 1-[(diiodomethyl)-sulphonyl]-4-methyl-benzene,

[0436]1-[[2-(2,4-dichlorophenyl)-1,3-dioxolan-2-yl]-methyl]-1H-imidazole,

[0437]1-[[2-(4-chlorophenyl)-3-phenyloxiranyl]-methyl]-1H-1,2,4-triazole,

[0438]1-[1-[2-[(2,4-dichlorophenyl)-methoxy]-phenyl]-ethenyl]-1H-imidazole,

[0439] 1-methyl-5-nonyl-2-(phenylmethyl)-3-pyrrolidinole,

[0440]2′,6′-dibromo-2-methyl-4′-trifluoromethoxy-4′-trifluoro-methyl-1,3-thiazole-5-carboxanilide,

[0441]2,2-dichloro-N-[1-(4-chlorophenyl)-ethyl]-1-ethyl-3-methyl-cyclopropane-carboxamide,

[0442] 2,6-dichloro-5-(methylthio)-4-pyrimidinyl-thiocyanate,

[0443] 2,6-dichloro-N-(4-trifluoromethylbenzyl)-benzamide,

[0444] 2,6-dichloro-N-[[4-(trifluoromethyl)-phenyl]-methyl]-benzamide,

[0445] 2-(2,3,3-triiodo-2-propenyl)-2H-tetrazole,

[0446]2-[(1-methylethyl)-sulphonyl]-5-(trichloromethyl)-1,3,4-thiadiazole.

[0447] 2-[[6-deoxy-4-O-(4-O-methyl-β-D-glycopyranosyl)-α-D-glucopyranosyl]-amino]-4-methoxy-1H-pyrrolo[2,3-d]pyrimidine-5-carbonitrile,

[0448] 2-aminobutane,

[0449] 2-bromo-2-(bromomethyl)-pentanedinitrile,

[0450]2-chloro-N-(2,3-dihydro-1,1,3-trimethyl-1H-inden-4-yl)-3-pyridinecarboxamide,

[0451]2-chloro-N-(2,6-dimethylphenyl)-N-(isothiocyanatomethyl)-acetamide,

[0452] 2-phenylphenol (OPP),

[0453] 3,4-dichloro-1-[4-(difluoromethoxy)-phenyl]-1H-pyrrole-2,5-dione,

[0454]3,5-dichloro-N-[cyano[(1-methyl-2-propinyl)-oxy]-methyl]-benzamide,

[0455] 3-( 1,1-dimethylpropyl-1-oxo-1H-indene-2-carbonitrile,

[0456] 3-[2-(4-chlorophenyl)-5-ethoxy-3-isoxazolidinyl]-pyridine,

[0457]4-chloro-2-cyano-N,N-dimethyl-5-(4-methylphenyl)-1H-imidazole-1-sulphonamide,

[0458] 4-methyl-tetrazolo[1,5-a]quinazolin-5(4H)-one,

[0459]8-(1,1-dimethylethyl)-N-ethyl-N-propyl-1,4-dioxaspiro[4.5]decane-2-methanamine,

[0460] 8-hydroxyquinoline sulphate,

[0461] 9H-xanthene-2-[(phenylamino)-carbonyl]-9-carboxylic hydrazide,

[0462]bis-(1-methylethyl)-3-methyl-4-[(3-methylbenzoyl)-oxy]-2,5-thiophenedicarboxylate,

[0463] cis-1-(4-chlorophenyl)-2-(1H-1,2,4-triazol-1-yl)-cycloheptanol,

[0464]cis-4-[3-[4-(1,1-dimethylpropyl)-phenyl-2-methylpropyl]-2,6-dimethyl-morpholine-hydrochloride,

[0465] ethyl [(4-chlorophenyl)-azo]-cyanoacetate,

[0466] potassium hydrogen carbonate,

[0467] methanetetrathiol sodium salt,

[0468] methyl1-(2,3-dihydro-2,2-dimethyl-1H-inden-1-yl)-1H-imidazole-5-carboxylate,

[0469] methylN-(2,6-dimethylphenyl)-N-(5-isoxazolylcarbonyl)-DL-alaninate,

[0470] methyl N-(chloroacetyl)-N-(2,6-dimethylphenyl)-DL-alaninate,

[0471] N-(2,3-dichloro-4-hydroxyphenyl)-1-methyl-cyclohexanecarboxamide,

[0472]N-(2,6-dimethylphenyl)-2-methoxy-N-(tetrahydro-2-oxo-3-furanyl)-acetamide,

[0473]N-(2,6-dimethylphenyl)-2-methoxy-N-(tetrahydro-2-oxo-3-thienyl)-acetamide,

[0474] N-(2-chloro-4-nitrophenyl)-4-methyl-3-nitro-benzenesulphonamide,

[0475] N-(4-cyclohexylphenyl)-1,4,5,6-tetrahydro-2-pyrimidinamine,

[0476] N-(4-hexylphenyl)-1,4,5,6-tetrahydro-2-pyrimidinamine,

[0477]N-(5-chloro-2-methylphenyl)-2-methoxy-N-(2-oxo-3-oxazolidinyl)-acetamide,

[0478] N-(6-methoxy-3-pyridinyl)-cyclopropanecarboxamide,

[0479] N-[2,2,2-trichloro-1-[(chloroacetyl)-amino]-ethyl]-benzamide,

[0480]N-[3-chloro-4,5-bis-(2-propinyloxy)-phenyl]-N′-methoxy-methanimidamide,

[0481] N-formyl-N-hydroxy-DL-alanine sodium salt,

[0482] O,O-diethyl[2-(dipropylamino)-2-oxoethyl]-ethylphosphoramidothioate,

[0483] O-methyl S-phenyl phenylpropylphosphoramidothioate,

[0484] S-methyl 1,2,3-benzothiadiazole-7-carbothioate,

[0485] spiro[2H]-1-benzopyran-2,1′(3′H)-isobenzofuran]-3′-one,

[0486] 4-[3,4-dimethoxyphenyl-3-(4-fluorophenyl)-acryloxy]-morpholine.

[0487] Bactericides

[0488] bronopol, dichlorophen, nitrapyrin, nickeldimethyldithiocarbamate, kasugamycin, octhilinone, furancarboxylic acid,oxytetracyclin, probenazole, streptomycin, tecloftalam, copper sulphateand other copper preparations.

[0489] Insecticides/Acaricides/Nematicides

[0490] abamectin, acephate, acetamiprid, acrinathrin, alanycarb,aldicarb, aldoxycarb, alpha-cypernethrin, alphamethrin, amitraz,avermectin, AZ 60541, azadirachtin, azamethiphos, azinphos A, azinphosM, azocyclotin,

[0491]Bacillus popilliae, Bacillus sphaericus, Bacillus subtilis,Bacillus thuringiensis, baculoviruses, Beauveria bassiana, Beauveriatenella, bendiocarb, benfuracarb, bensultap, benzoximate,betacyfluthrin, bifenazate, bifenthrin, bioethanomethrin, biopermethrin,bistrifluorone, BPMC, bromophos A, bufencarb, buprofezin, butathiofos,butocarboxim, butylpyridaben,

[0492] cadusafos, carbaryl, carbofuran, carbophenothion, carbosulfan,cartap, chloethocarb, chlorethoxyfos, chlorfenapyr, chlorfenvinphos,chlorfluazuron, chlormephos, chlorpyrifos, chlorpyrifos M,chlovaporthrin, chromafenozide, cis-resmethrin, cispermethrin,clocythrin, cloethocarb, clofentezine, clothianidine, cyanophos,cycloprene, cycloprothrin, cyfluthrin, cyhalothrin, cyhexatin,cypermethrin, cyromazine,

[0493] deltamethrin, demeton M, demeton S, demeton-S-methyl,diafenthiuron, diazinon, dichlorvos, dicofol, diflubenzuron, dimethoate,dimethylvinphos, diofenolan, disulfoton, docusat-sodium, dofenapyn,

[0494] eflusilanate, emamectin, empenthrin, endosulfan, Entomopfthoraspp., esfenvalerate, ethiofencarb, ethion, ethoprophos, etofenprox,etoxazole, etrimfos,

[0495] fenamiphos, fenazaquin, fenbutatin oxide, fenitrothion,fenothiocarb, fenoxacrim, fenoxycarb, fenpropathrin, fenpyrad,fenpyrithrin, fenpyroximate, fenvalerate, fipronil, fluazinam,fluazuron, flubrocythrinate, flucycloxuron, flucythrinate, flufenoxuron,flumethrin, flutenzine, fluvalinate, fonophos, fosmethilan, fosthiazate,fubfenprox, furathiocarb,

[0496] granulosis viruses,

[0497] halofenozide, HCH, heptenophos, hexaflumuron, hexythiazox,hydroprene, imidacloprid, indoxacarb, isazofos, isofenphos, isoxathion,ivermectin, lambda-cyhalothrin, lufenuron,

[0498] malathion, mecarbam, metaldehyde, methamidophos, Metharhiziumanisopliae, Metharhizium flavoviride, methidathion, methiocarb,methoprene, methomyl, methoxyfenozide, metolcarb, metoxadiazone,mevinphos, milbemectin, rilbemycin, monocrotophos,

[0499] naled, nitenpyram, nithiazine, novaluron, nuclear polyhedrosisviruses, omethoat, oxamyl, oxydemethon M,

[0500]Paecilomyces fumosoroseus, parathion A, parathion M, permethrin,phenthoate, phorate, phosalone, phosmet, phosphamidon, phoxim,pirimicarb, pirimiphos A, pirimiphos M, profenofos, promecarb,propargite, propoxur, prothiofos, prothoate, pymetrozine, pyraclofos,pyresmethrin, pyrethrum, pyridaben, pyridathion, pyrimidifen,pyriproxyfen,

[0501] quinalphos,

[0502] ribavirin,

[0503] salithion, sebufos, silafluofen, spinosad, spirodiclofen,sulfotep, sulprofos, tau-fluvalinate, tebufenozide, tebufenpyrad,tebupirimiphos, teflubenzuron, tefluthrin, temephos, temivinphos,terbufos, tetrachlorvinphos, tetradifon, theta-cypermethrin,thiacloprid, thiamethoxam, thiapronil, thiatriphos, thiocyclam hydrogenoxalate, thiodicarb, thiofanox, thuringiensin, tralocythrin,tralomethrin, triarathene, triazamate, triazophos, triazuron,trichlophenidine, trichlorfon, triflumuron, trimethacarb,

[0504] vamidothion, vaniliprole, Verticillium lecanii,

[0505] YI 5302,

[0506] zeta-cypermethrin, zolaprofos

[0507](1R-cis)-[5-(phenylmethyl)-3-furanyl]-methyl-3-[(dihydro-2-oxo-3(2H)-furanylidene)-methyl]-2,2-dimethylcyclopropanecarboxylate (3-phenoxyphenyl)-methyl-2,2,3,3-tetramethylcyclopropanecarboxylate1-[(2-chloro-5-thiazolyl)methyl]tetrahydro-3,5-dimethyl-N-nitro-1,3,5-triazine-2(1H)-imine

[0508]2-(2-chloro-6-fluorophenyl)-4-[4-(1,1-dimethylethyl)phenyl]-4,5-dihydro-oxazole

[0509] 2-(acetlyoxy)-3-dodecyl-1,4-naphthalenedione

[0510]2-chloro-N-[[[4-(1-phenylethoxy)-phenyl]-amino]-carbonyl]-benzamide

[0511]2-chloro-N-[[[4-(2,2-dichloro-1,1-difluoroethoxy)-phenyl]-amino]-carbonyl]-benzamide

[0512] 3-methylphenyl propylcarbamate

[0513] 4-[4-(4-ethoxyphenyl)-4-methylpentyl]-1-fluoro-2-phenoxy-benzene

[0514]4-chloro-2-(1,1-dimethylethyl)-5-[[2-(2,6-dimethyl-4-phenoxyphenoxy)ethyl]thio]-3(2H)-pyridazinone

[0515]4-chloro-2-(2-chloro-2-methylpropyl)-5-[(6-iodo-3-pyridinyl)methoxy]-3(2H)-pyridazinone

[0516]4-chloro-5-[(6-chloro-3-pyridinyl)methoxy]-2-(3,4-dichlorophenyl)-3(2H)-pyridazinone

[0517]Bacillus thuringiensis strain EG-2348

[0518] [2-benzoyl-1-(1,1-dimethylethyl)-hydrazinobenzoic acid

[0519]2,2-dimethyl-3-(2,4-dichlorophenyl)-2-oxo-1-oxaspiro[4.5]dec-3-en-4-ylbutanoate

[0520] [3-[(6-chloro-3-pyridinyl)methyl]-2-thiazolidinylidene]-cyanamide

[0521] dihydro-2-(nitromethylene)-2H-1,3-thiazine-3(4H)-carboxaldehyde

[0522] ethyl[2-[[1,6-dihydro-6-oxo-1-(phenylmethyl)-4-pyridazinyl]oxy]ethyl]-carbamate

[0523] N-(3,4,4-trifluoro-1-oxo-3-butenyl)-glycine

[0524]N-(4-chlorophenyl)-3-[4-(difluoromethoxy)phenyl]-4,5-dihydro-4-phenyl-1H-pyrazole-1-carboxamide

[0525] N-[(2-chloro-5-thiazolyl)methyl]-N′-methyl-N″-nitro-guanidine

[0526] N-methyl-N′-(1-methyl-2-propenyl)-1,2-hydrazinedicarbothioamide

[0527] N-methyl-N′-2-propenyl-1,2-hydrazinedicarbothioamide

[0528] O,O-diethyl[2-(dipropylamino)-2-oxoethyl]-ethylphosphoramidothioate.

[0529] N-cyanomethyl-4-trifluoromethyl-nicotinamide

[0530]3,5-dichloro-1-(3,3-dichloro-2-propenyloxy)-4-[3-(5-trifluoromethyl-pyridin-2-yloxy)-propoxy]-benzene.

[0531] Mixtures with other known active compounds such as herbicides orwith fertilizers and growth regulators are also possible.

[0532] When used as insecticides, the active compounds according to theinvention can furthermore be present in their commercially availableformulations and in the use forms, prepared from these formulations, asa mixture with synergists. Synergists are compounds which increase theaction of the active compounds, without it being necessary for thesynergist added to be active itself.

[0533] The active compound content of the use forms prepared from thecommercially available formulations can vary within wide limits. Theactive compound concentration of the use forms can be from 0.0000001 to95% by weight of active compound, preferably between 0.0001 and 1% byweight.

[0534] The compounds are employed in a customary manner appropriate forthe use forms. When used against hygiene pests and stored-product pests,the active compound is distinguished by an excellent residual action onwood and clay as well as good stability to alkali on limed substrates.

[0535] The active compounds according to the invention are not onlyactive against plant pests, hygiene pests and stored-product pests, butalso, in the veterinary medicine sector, against animal parasites(ectoparasites) such as hard ticks, soft ticks, mange mites, harvestmites, flies (stinging and licking), parasitizing fly larvae, lice, hairlice, bird lice and fleas. These parasites include:

[0536] From the order of the Anoplurida, for example, Haematopinus spp.,Linognathus spp., Pediculus spp., Phtirus spp., Solenopotes spp.

[0537] From the order of the Mallophagida and the suborders Amblycerinaand Ischnocerina, for example, Trimenopon spp., Menopon spp., Trinotonspp., Bovicola spp., Werneckiella spp., Lepikentron spp., Damalina spp.,Trichodectes spp., Felicola spp.

[0538] From the order Diptera and the suborders Nematocerina andBrachycerina, for example, Aedes spp., Anopheles spp., Culex spp.,Simulium spp., Eusimulium spp., Phlebotomus spp., Lutzomyia spp.,Culicoides spp., Chrysops spp., Hybomitra spp., Atylotus spp., Tabanusspp., Haematopota spp., Philipomyia spp., Braula spp., Musca spp.,Hydrotaea spp., Stomoxys spp., Haematobia spp., Morellia spp., Fanniaspp., Glossina spp., Calliphora spp., Lucilia spp., Chrysomyia spp.,Wohlfahrtia spp., Sarcophaga spp., Oestrus spp., Hypoderma spp.,Gasterophilus spp., Hippobosca spp., Lipoptena spp., Melophagus spp.

[0539] From the order of the Siphonapterida, for example, Pulex spp.,Ctenocephalides spp., Xenopsylla spp., Ceratophyllus spp.

[0540] From the order of the Heteroptcnlda, for example, Cimex spp.,Triatoma spp., Rhodnius spp., Panstmongylus spp.

[0541] From the order of the Blattarida, for example, Blatta orientalis,Periplaneta americana, Blattela germanica, Supella spp.

[0542] From the subclass of the Acaria (Acarida) and the orders of theMeta- and Mesostigmata, for example, Argas spp., Ornithodorus spp.,Otobius spp., Ixodes spp., Amblyomma spp., Boophilus spp., Dermacentorspp., Haemophysalis spp., Hyalomma spp., Rhipicephalus spp., Dermanyssusspp., Raillietia spp., Pneumonyssus spp., Sternostoma spp., Varroa spp.

[0543] From the order of the Actinedida (Prostigmata) and Acaridida(Astigmata), for example, Acarapis spp., Cheyletiella spp.,Omithocheyletia spp., Myobia spp., Psorergates spp., Demodex spp.,Trombicula spp., Listrophorus spp., Acarus spp., Tyrophagus spp.,Caloglyphus spp., Hypodectes spp., Pterolichus spp., Psoroptes spp.,Chorioptes spp., Otodectes spp., Sarcoptes spp., Notoedres spp.,Knemidocoptes spp., Cytodites spp., Laminosioptes spp.

[0544] The active compounds according to the invention are also suitablefor controlling arthropods which attack agricultural livestock such as,for example, cattle, sheep, goats, horses, pigs, donkeys, camels,buffaloes, rabbits, chickens, turkeys, ducks, geese, honey-bees, otherdomestic animals such as, for example, dogs, cats, caged birds, aquariumfish and so-called experimental animals such as, for example, hamsters,guinea pigs, rats and mice. By controlling these arthropods, cases ofdeath and reductions in productivity (for meat, milk, wool, hides, eggs,honey and the like) should be diminished, so that more economical andsimpler animal husbandry is possible by the use of the active compoundsaccording to the invention.

[0545] The active compounds according to the invention are used in theveterinary sector in a known manner by enteral administration in theform of, for example, tablets, capsules, potions, drenches, granules,pastes, boluses, the feed-through method, suppositories, by parenteraladministration such as, for example, by injections (intramuscularly,subcutaneously, intravenously, intraperitoneally and the like),implants, by nasal administration, by dermal administration in the formof, for example, immersing or dipping, spraying, pouring-on,spotting-on, washing, dusting, and with the aid ofactive-compound-comprising moulded articles such as collars, ear tags,tail tags, limb bands, halters, marking devices and the like.

[0546] When used for cattle, poultry, domestic animals and the like, theactive compounds can be applied as formulations (for example powders,emulsions, flowables) comprising the active compounds in an amount of 1to 80% by weight, either directly or after 100- to 10 000-fold dilution,or they may be used as a chemical dip.

[0547] Moreover, it has been found that the active compounds accordingto the invention show a potent insecticidal action against insects whichdestroy industrial materials.

[0548] The following insects may be mentioned by way of example and withpreference, but not by way of limitation:

[0549] Beetles such as

[0550]Hylotrupes bajulus, Chlorophorus pilosis, Anobium punctatum,Xestobium rufovillosum, Ptilinus pecticornis, Dendrobium pertinex,Ernobius mollis, Priobium carpini, Lyctus brunneus, Lyctus africanus,Lyctus planicollis, Lyctus linearis, Lyctus pubescens, Trogoxylonaequale, Minthes rugicollis, Xyleborus spec., Tryptodendron spec., Apatemonachus, Bostrychus capucins, Heterobostrychus brunneus, Sinoxylonspec., Dinoderus minutus.

[0551] Dermapterans such as

[0552]Sirex juvencus, Urocerus gigas, Urocerus gigas taignus, Urocerusaugur.

[0553] Termites such as

[0554]Kalotermes flavicollis, Cryptotermes brevis, Heterotermesindicola, Reticulitermes flavipes, Reticulitermes santonensis.Reticulitermes lucifugus, Mastotermes darwiniensis, Zootermopsisnevadensis, Coptotermes formosanus.

[0555] Bristle-tails such as Lepisma saccharina.

[0556] Industrial materials in the present context are understood asmeaning non-living materials such as, preferably, polymers, adhesives,glues, paper and board, leather, wood, timber products and paints.

[0557] The materials which are to be protected from insect attack isvery especially preferably wood and timber products.

[0558] Wood and timber products which can be protected by thecomposition according to the invention, or mixtures comprising it, areto be understood as meaning, for example:

[0559] construction timber, wooden beams, railway sleepers, bridgecomponents, jetties, vehicles made of wood, boxes, pallets, containers,telephone poles, wood lagging, windows and doors made of wood, plywood,chipboard, joinery, or timber products which quite generally are used inhouse construction or building joinery.

[0560] The active compounds can be used as such, in the form ofconcentrates or generally customary formulations such as powders,granules, solutions, suspensions, emulsions or pastes. Theabovementioned formulations can be prepared in a manner known per se,for

[0561] example by mixing the active compounds with at least one solventor diluent, emulsifier, dispersant and/or binder or fixative, waterrepellant, if desired desiccants and UV stabilizers, and if desiredcolorants and pigments and other processing auxiliaries.

[0562] The insecticidal compositions or concentrates used for protectingwood and timber products comprise the active compound according to theinvention in a concentration of 0.0001 to 95% by weight, in particular0.001 to 60% by weight.

[0563] The amount of composition or concentrate employed depends on thespecies and the abundance of the insects and on the medium. The optimalquantity to be employed can be determined in each case by test seriesupon application. In general, however, it will suffice to employ 0.0001to 20% by weight, preferably 0.001 to 10% by weight, of the activecompound, based on the material to be protected.

[0564] A suitable solvent and/or diluent is an organochemical solvent orsolvent mixture and/or an oily or oil-type organochemical solvent orsolvent mixture of low volatility and/or a polar organochemical solventor solvent mixture and/or water and, if appropriate, an emulsifierand/or wetter.

[0565] Organochemical solvents which are preferably employed are oily oroil-type solvents with an evaporation number of above 35 and a flashpoint of above 30° C., preferably above 45° C. Such oily and oil-typesolvents which are insoluble in water and of low volatility and whichare used are suitable mineral oils or their aromatic fractions ormineral-oil-containing solvent mixtures, preferably white spirit,petroleum and/or alkylbenzene.

[0566] Mineral oils with a boiling range of 170 to 220° C., white spiritwith a boiling range of 170 to 220° C., spindle oil with a boiling rangeof 250 to 350° C., petroleum and aromatics with a boiling range of 160to 280° C., oil of terpentine, and the like are advantageously used.

[0567] In a preferred embodiment, liquid aliphatic hydrocarbons with aboiling range of 180 to 210° C. or high-boiling mixtures of aromatic andaliphatic hydrocarbons with a boiling range of 180 to 220° C. and/orspindle oil and/or monochloronaphthalene, preferably(x-monochloronaphthalene are used.

[0568] The organic oily or oil-type solvents of low volatility and withan evaporation number of above 35 and a flash point of above 30° C.,preferably above 45° C., can be replaced in part by organochemicalsolvents of high or medium volatility, with the proviso that the solventmixture also has an evaporation number of above 35 and a flash point ofabove 30° C., preferably above 45° C., and that theinsecticide-fungicide mixture is soluble or emulsifiable in this solventmixture.

[0569] In a preferred embodiment, some of the organochemical solvent orsolvent mixture is replaced by an aliphatic polar organochemical solventor solvent mixture. Aliphatic organochemical solvents which containhydroxyl and/or ester and/or ether groups are preferably used, such as,for example, glycol ethers, esters or the like.

[0570] Organochemical binders used for the purposes of the presentinvention are the synthetic resins and/or binding drying oils which areknown per se and which can be diluted in water and/or dissolved ordispersed or emulsified in the organochemical solvents employed, inparticular binders composed of, or comprising, an acrylate resin, avinyl resin, for example polyvinyl acetate, polyester resin,polycondensation or polyaddition resin, polyurethane resin, alkyd resinor modified alkyd resin, phenol resin, hydrocarbon resin such asindene/coumarone resin, silicone resin, drying vegetable and/or dryingoils and/or physically drying binders based on a natural and/orsynthetic resin.

[0571] The synthetic resin employed as binder can be employed in theform of an emulsion, dispersion or solution. Bitumen or bituminoussubstances may also be used as binders, in amounts of up to 10% byweight. In addition, colorants, pigments, water repellants,odour-masking agents, and inhibitors or anticorrosive agents and thelike, all of which are known per se, can be employed.

[0572] In accordance with the invention, the composition or theconcentrate preferably comprises, as organochemical binders, at leastone alkyd resin or modified alkyd resin and/or a drying vegetable oil.Alkyd resins which are preferably used in accordance with the inventionare those with an oil content of over 45% by weight, preferably 50 to68% by weight.

[0573] Some or all of the abovementioned binder can be replaced by afixative (mixture) or plasticizer (mixture). These additives areintended to prevent volatilization of the active compounds, and alsocrystallization or precipitation. They preferably replace 0.01 to 30% ofthe binder (based on 100% of binder employed).

[0574] The plasticizers are from the chemical classes of the phthalicesters, such as dibutyl phthalate, dioctyl phthalate or benzyl butylphthalate, phosphoric esters such as tributyl phosphate, adipic esterssuch as di-(2-ethylhexyl)-adipate, stearates such as butyl stearate oramyl stearate, oleates such as butyl oleate, glycerol ethers orhigher-molecular-weight glycol ethers, glycerol esters andp-toluenesulphonic esters.

[0575] Fixatives are based chemically on polyvinyl alkyl ethers such as,for example, polyvinyl methyl ether, or ketones such as benzophenone andethylenebenzophenone.

[0576] Other suitable solvents or diluents are, in particular, water, ifappropriate as a mixture with one or more of the abovementionedorganochemical solvents or diluents, emulsifiers and dispersants.

[0577] Particularly effective timber protection is achieved byindustrial-scale impregnating processes, for example the vacuum,double-vacuum or pressure processes.

[0578] The ready-to-use compositions can also comprise otherinsecticides, if appropriate, and also one or more fungicides, ifappropriate.

[0579] Possible additional mixing components are, preferably, theinsecticides and fungicides mentioned in WO 94/29 268. The compoundsmentioned in this document are an explicit constituent of the presentapplication.

[0580] Especially preferred mixing partners which may be mentioned areinsecticides, such as chlorpyriphos, phoxim, silafluofin, alphamethrin,cyfluthrin, cypermethrin, deltamethrin, permethrin, imidacloprid, NI-25,flufenoxuron, hexaflumuron, transfluthrin, thiacloprid, methoxyfenozideand triflumuron,

[0581] and also fungicides, such as epoxyconazole, hexaconazole,azaconazole, propiconazole, tebuconazole, cyproconazole, metconazole,imazalil, dichlorfluanid, tolylfluanid, 3-iodo-2-propinyl-butylcarbamate, N-octyl-isothiazolin-3-one and4,5-dichloro-N-octylisothiazolin-3-one.

[0582] The combinations according to the invention can at the same timebe employed for protecting objects which come into contact withsaltwater or brackish water, such as hulls, screens, nets, buildings,moorings and signalling systems, against fouling.

[0583] Fouling by sessile Oligochaeta, such as Serpulidae, and by shellsand species from the Ledamorpha group (goose barnacles), such as variousLepas and Scalpellum 30 species, or by species from the Balanomorphagroup (acorn barnacles), such as Balanus or Pollicipes species,increases the frictional drag of ships and, as a consequence, leads to amarked increase in operation costs owing to higher energy consumptionand additionally frequent residence in the dry dock.

[0584] Apart from fouling by algae, for example Ectocarpus sp. andCeramium sp., fouling by sessile Entomostraka groups, which come underthe generic term Cirripedia (cirriped crustaceans), is of particularimportance.

[0585] Surprisingly, it has now been found that the compounds accordingto the invention, alone or in combination with other active compounds,have an outstanding antifouling action.

[0586] Using the combinations according to the invention, alone or incombination with other active compounds, allows the use of heavy metalssuch as, for example, in bis(trialkyltin) sulphides, tri-n-butyltinlaurate, tri-n-butyltin chloride, copper(I) oxide, triethyltin chloride,tri-n-butyl(2-phenyl-4-chlorophenoxy)tin, tributyltin oxide, molybdenumdisulphide, antimony oxide, polymeric butyl titanate,phenyl-(bispyridine)-bismuth chloride, tri-n-butyltin fluoride,manganese ethylenebisthiocarbamate, zinc dimethyldithiocarbamate, zincethylenebisthiocarbamate, zinc salts and copper salts of 2-pyridinethiol1-oxide, bisdimethyldithiocarbamoylzinc ethylene-bisthiocarbamate, zincoxide, copper(I) ethylene-bisdithiocarbamate, copper thiocyanate, coppernaphthenate and tributyltin halides to be dispensed with, or theconcentration of these compounds substantially reduced.

[0587] If appropriate, the ready-to-use antifouling paints canadditionally comprise other active compounds, preferably algicides,fungicides, herbicides, molluscicides, or other antifouling activecompounds.

[0588] Preferably suitable components in combinations with theantifouling compositions according to the invention are:

[0589] algicides such as

[0590] 2-tert-butylamino-4-cyclopropylamino-6-methylthio-1,3,5-triazine,dichlorophen, diuron, endothal, fentin acetate, isoproturon,methabenzthiazuron, oxyfluorfen, quinoclamine and terbutryn;

[0591] fungicides such as

[0592] benzo[b]thiophenecarboxylic acid cyclohexylamide S,S-dioxide,dichlofluanid, fluorfolpet, 3-iodo-2-propinyl butylcarbamate,tolylfluanid and azoles such as azaconazole, cyproconazole,epoxyconazole, hexaconazole, metconazole, propiconazole andtebuconazole;

[0593] molluscicides such as

[0594] fentin acetate, metaldehyde, methiocarb, niclosamid, thiodicarband trimethacarb;

[0595] or conventional antifouling active compounds such as

[0596] 4,5-dichloro-2-octyl-4-isothiazolin-3-one, diiodomethylparatrylsulphone, 2-(N,N-dimethylthiocarbamoylthio)-5-nitrothiazyl, potassium,copper, sodium and zinc salts of 2-pyridinethiol 1-oxide,pyridine-triphenylborane, tetrabutyldistannoxane,2,3,5,6-tetrachloro-4-(methylsulphonyl)-pyridine,2,4,5,6-tetrachloroisophthalonitrile, tetramethylthiuram disulphide and2,4,6-trichlorophenylmaleiimide.

[0597] The antifouling compositions used comprise the active compoundaccording to the invention of the compositions according to theinvention in a concentration of 0.001 to 50% by weight, in particular0.01 to 20% by weight.

[0598] Moreover, the antifouling compositions according to the inventioncomprise the customary components such as, for example, those describedin Ungerer, Chem. Ind. 1985, 37, 730-732 and Williams, AntifoulingMarine Coatings, Noyes, Park Ridge, 1973.

[0599] Besides the algicidal, fungicidal, molluscicidal active compoundsand insecticidal active compounds according to the invention,antifouling paints comprise, in particular, binders.

[0600] Examples of recognized binders are polyvinyl chloride in asolvent system, chlorinated rubber in a solvent system, acrylic resinsin a solvent system, in particular in an aqueous system, vinylchloride/vinyl acetate copolymer systems in the form of aqueousdispersions or in the form of organic solvent systems,butadiene/styrene/acrylonitrile rubbers, drying oils such as linseedoil, resin esters or modified hardened resins in combination with tar orbitumens, asphalt and epoxy compounds, small amounts of chlorine rubber,chlorinated polypropylene and vinyl resins.

[0601] If appropriate, paints also comprise inorganic pigments, organicpigments or colorants which are preferably insoluble in salt water.Paints may furthermore comprise materials such as colophonium to allowcontrolled release of the active compounds. Furthermore, the paints maycomprise plasticizers, modifiers which affect the rheological propertiesand other conventional constituents. The compounds according to theinvention or the abovementioned mixtures may also be incorporated intoself-polishing antifouling systems.

[0602] The active compounds are also suitable for controlling animalpests, in particular insects, arachnids and mites, which are found inenclosed spaces such as, for example, dwellings, factory halls, offices,vehicle cabins and the like. They can be employed alone or incombination with other active compounds and excipients in domesticinsecticide products for controlling these pests. They are activeagainst sensitive and resistant species and against all developmentalstages. These pests include:

[0603] From the order of the Scorpionidea, for example, Buthusoccitanus.

[0604] From the order of the Acarina, for example, Argas persicus, Argasreflexus, Bryobia spp., Dermanyssus gallinae, Glyciphagus domesticus,Ornithodorus moubat, Rhipicephalus sanguineus, Trombicula alfreddugesi,Neutrombicula autumnalis, Dermatophagoides pteronissimus,Dermatophagoides forinae.

[0605] From the order of the Araneae, for example, Aviculariidae,Araneidae.

[0606] From the order of the Opiliones, for example, Pseudoscorpioneschelifer, Pseudoscorpiones cheiridium, Opiliones phalangium.

[0607] From the order of the Isopoda, for example, Oniscus asellus,Porcellio scaber.

[0608] From the order of the Diplopoda, for example, Blaniulusguttulatus, Polydesmus spp.

[0609] From the order of the Chilopoda, for example, Geophilus spp.

[0610] From the order of the Zygentoma, for example, Ctenolepisma spp.,Lepisma saccharina, Lepismodes inquilinus.

[0611] From the order of the Blattaria, for example, Blatta orientalies,Blattella germanica, Blattella asahinai, Leucophaea maderae, Panchloraspp., Parcoblatta spp., Periplaneta australasiae, Periplaneta americana,Periplaneta brunnea, Periplaneta fuliginosa, Supella longipalpa.

[0612] From the order of the Saltatoria, for example, Acheta domesticus.

[0613] From the order of the Dermaptera, for example, Forficulaauricularia.

[0614] From the order of the Isoptera, for example, Kalotermes spp.,Reticulitermes spp.

[0615] From the order of the Psocoptera, for example, Lepinatus spp.,Liposcelis spp.

[0616] From the order of the Coleptera, for example, Anthrenus spp.,Attagenus spp., Dermestes spp., Latheticus oryzae, Necrobia spp., Ptinusspp., Rhizopertha dominica, Sitophilus granarius, Sitophilus oryzae,Sitophilus zeamais, Stegobium paniceum.

[0617] From the order of the Diptera, for example,

[0618] Aedes aegypti, Aedes albopictus, Aedes taeniorhynchus, Anophelesspp., Calliphora erythrocephala, Chrysozona pluvialis, Culexquinquefasciatus, Culex pipiens, Culex tarsalis, Drosophila spp., Fanniacanicularis, Musca domestica, Phlebotomus spp., Sarcophaga camaria,Simulium spp., Stomoxys calcitrans, Tipula paludosa.

[0619] From the order of the Lepidoptera, for example, Achroia grisella,Galleria mellonella, Plodia interpunctella, Tinea cloacella, Tineapellionella, Tineola bisselliella.

[0620] From the order of the Siphonaptera, for example, Ctenocephalidescanis, Ctenoccphalides felis, Pulex irritans, Tunga penetrans,Xenopsylla cheopis.

[0621] From the order of the Hymenoptera, for example, Camponlotusherculcanus, Lasius fuliginosus, Lasius niger, Lasius umbratus,Monomorium pharaonis, Paravespula spp., Tetramorium caespitum.

[0622] From the order of the Anoplura, for example, Pediculus humanuscapitis, Pediculus humanus corporis, Phthirus pubis.

[0623] From the order of the Heteroptera, for example, Cimex hemipterus,Cimex lectularius, Rhodinus prolixus, Triatoma infestans.

[0624] In the field of household insecticides, they are used alone or incombination with other suitable active compounds, such as phosphoricacid esters, carbamates, pyrethroids, growth regulators or activecompounds from other known classes of insecticides.

[0625] They are used as aerosols, pressure-free spray products, forexample pump and atomizer sprays, automatic fogging systems, foggers,foams, gels, evaporator products with evaporator tablets made ofcellulose or polymer, liquid evaporators, gel and membrane evaporators,propeller-driven evaporators, energy-free, or passive, evaporationsystems, moth papers, moth bags and moth gels, as granules or dusts, inbaits for spreading or in bait stations.

[0626] The active compounds according to the invention can be used asdefoliants, desiccants, haulm killers and, especially, as weed killers.Weeds in the broadest sense are understood to mean all plants which growin locations where they are undesired. Whether the substances accordingto the invention act as total or selective herbicides dependsessentially on the amount used.

[0627] The active compounds according to the invention can be used, forexample, in connection with the following plants:

[0628] Dicotyledonous weeds of the genera: Abutiloin, Amaranthus,Ambrosia, Anoda, Anthemis, Aphanes, Atriplex, Bellis, Bidens, Capsella,Carduus, Cassia, Centaurea, Chenopodium, Cirsium, Convolvulus, Datura,Desmodium, Emex, Erysimum, Euphorbia, Galeopsis, Galinsoga, Galium,Hibiscus, Ipomoea, Kochia, Lamium, Lepidium, Lindernia, Matricaria,Mentha, Mercurialis, Mullugo, Myosotis, Papaver, Pharbitis, Plantago,Polygonum, Portulaca, Ranunculus, Raphanus, Rorippa, Rotala, Rumex,Salsola, Senecio, Sesbania, Sida, Sinapis, Solanum, Sonchus, Sphenoclea,Stellaria, Taraxacum, Thlaspi, Trifolium, Urtica, Veronica, Viola,Xanthium.

[0629] Dicotyledonous crops of the genera: Arachis, Beta, Brassica,Cucumis, Cucurbita, Helianthus, Daucus, Glycine, Gossypium, Ipomoea,Lactuca, Linum, Lycopersicon, Nicotiana, Phaseolus, Pisum, Solanum,Vicia.

[0630] Monocotyledonous weeds of the genera: Aegilops, Agropyron,Agrostis, Alopecurus, Apera, Avena, Brachiaria, Bromus, Cenchrus,Commelina, Cynodon, Cyperus, Dactyloctenium, Digitaria, Echinochloa,Eleocharis, Eleusine, Eragrostis, Eriochloa, Festuca, Fimbristylis,Heteranthera, Imperata, Ischaemum, Leptochloa, Lolium, Monochoria,Panicum, Paspalum, Phalaris, Phleum, Poa, Rottboellia, Sagittaria,Scirpus, Setaria, Sorghum.

[0631] Monocotyledonous crops of the genera: Allium, Ananas, Asparagus,Avena, Hordeum, Oryza, Panicum, Saccharum, Secale, Sorghum, Triticale,Triticum, Zea.

[0632] However, the use of the active compounds according to theinvention is in no way restricted to these genera, but also extends inthe same manner to other plants.

[0633] The active compounds according to the invention are suitable,depending on the concentration, for the total control of weeds, forexample on industrial terrain and rail tracks, and on paths and areaswith and without tree plantings. Similarly, the active compoundsaccording to the invention can be employed for controlling weeds inperennial crops, for example forests, decorative tree plantings,orchards, vineyards, citrus groves, nut orchards, banana plantations,coffee plantations, tea plantations, rubber plantations, oil palmplantations, cocoa plantations, soft fruit plantings and hop fields, onlawns, turf and pastureland, and for the selective control of weeds inannual crops.

[0634] The compounds according to the invention have strong herbicidalactivity and a broad active spectrum when used on the soil and onabove-ground parts of plants. To a certain extent they are also suitablefor the selective control of monocotyledonous and dicotyledonous weedsin monocotyledonous and dicotyledonous crops, both by the pre-emergenceand by the post-emergence method.

[0635] At certain concentrations or application rates, the activecompounds according to the invention can also be employed forcontrolling animal pests and fungal or bacteria] plant diseases. Ifappropriate, they can also be used as intermediates or precursors forthe synthesis of other active compounds.

[0636] All plants and plant parts can be treated in accordance with theinvention. Plants are to be understood as meaning in the present contextall plants and plant populations such as desired and undesired wildplants or crop plants (including naturally occurring crop plants). Cropplants can be plants which can be obtained by conventional plantbreeding and optimization methods or by biotechnological and recombinantmethods or by combinations of these methods, including the transgenicplants and inclusive of the cultivars protectable or not protectable byplant breeders' rights. Plant parts are to be understood as meaning allparts and organs of plants above and below the ground, such as shoot,leaf, flower and root, examples which may be mentioned being leaves,needles, stalks, stems, flowers, fruit bodies, fruits, seeds, roots,tubers and rhizomes. The plant parts also include harvested material,and vegetative and generative propagation material, for examplecuttings, tubers, rhizomes, offsets and seeds.

[0637] Treatment according to the invention of the plants and plantparts with the active compounds is carried out directly or by allowingthe compounds to act on the surroundings, environment or storage spaceby the customary treatment methods, for example by immersion, spraying,evaporation, fogging, scattering, painting on and, in the case ofpropagation material, in particular in the case of seeds, also byapplying one or more coats.

[0638] As already mentioned above, it is possible to treat all plantsand their parts according to the invention. In a preferred embodiment,wild plant species and cultivars, or those obtained by conventionalbiological breeding, such as crossing or protoplast fusion, and partsthereof, are treated. In a further preferred embodiment, transgenicplants and cultivars obtained by genetical engineering, if appropriatein combination with conventional methods (Genetically ModifiedOrganisms), and parts thereof are treated. The term “parts” or “parts ofplants” or “plant parts” has been explained above.

[0639] Particularly preferably, plants of the cultivars which are ineach case commercially available or in use are treated according to theinvention. Cultivars are to be understood as meaning plants havingcertain properties (“traits”) and which have been obtained byconventional breeding, by mutagenesis or by recombinant DNA techniques.They can be varieties, bio- or genotypes.

[0640] Depending on the plant species or cultivars, their location andgrowth conditions (soils, climate, vegetation period, diet), thetreatment according to the invention may also result in superadditive(“synergistic”) effects. Thus, for example, reduced application ratesand/or a widening of the activity spectrum and/or an increase in theactivity of the substances and compositions which can be used accordingto the invention, better plant growth, increased tolerance to high orlow temperatures, increased tolerance to drought or to water or soilsalt content, increased flowering performance, easier harvesting,accelerated maturation, higher harvest yields, better quality and/or ahigher nutritional value of the harvested products, better storagestability and/or processability of the harvested products are possiblewhich exceed the effects which were actually to be expected.

[0641] The transgenic plants or cultivars (i.e. those obtained bygenetical engineering) which are preferably treated according to theinvention include all plants which, in the genetic modification,received genetic material which imparted particularly advantageoususeful properties (“traits”) to these plants. Examples of suchproperties are better plant growth, increased tolerance to high or lowtemperatures, increased tolerance to drought or to water or soil saltcontent, increased flowering performance, easier harvesting, acceleratedmaturation, higher harvest yields, better quality and/or a highernutritional value of the harvested products, better storage stabilityand/or processability of the harvested products. Further andparticularly emphasized examples of such properties are a better defenceof the plants against animal and microbial pests, such as againstinsects, mites, phytopathogenic fungi, bacteria and/or viruses, and alsoincreased tolerance of the plants to certain herbicidally activecompounds. Examples of transgenic plants which may be mentioned are theimportant crop plants, such as cereals (wheat, rice), maize, soya beans,potatoes, cotton, oilseed rape and also fruit plants (with the fruitsapples, pears, citrus fruits and grapes), and particular emphasis isgiven to maize, soya beans, potatoes, cotton and oilseed rape. Traitsthat are emphasized are in particular increased defence of the plantsagainst insects by toxins formed in the plants, in particular thoseformed in the plants by the genetic material from Bacillus thuringiensis(for example by the genes CryIA(a), CryIA(b), CryIA(c), CryIIA, CryIIIA,CryIIIB2, Cry9c Cry2Ab, Cry3Bb and CryIF and also combinations thereof)(hereinbelow referred to as “Bt plants”). Traits that are alsoparticularly emphasized are the increased defence of the plants tofungi, bacteria and viruses by systemic acquired resistance (SAR),systemin, phytoalexins, elicitors and resistance genes andcorrespondingly expressed proteins and toxins. Traits that arefurthermore particularly emphasized are the increased tolerance of theplants to certain herbicidally active compounds, for exampleimidazolinones, sulphonylureas, glyphosate or phosphinotricin (forexample the “PAT” gene). The genes which impart the desired traits inquestion can also be present in combination with one another in thetransgenic plants. Examples of “Bt plants” which may be mentioned aremaize varieties, cotton varieties, soya bean varieties and potatovarieties which are sold under the trade names YIELD GARD® (for examplemaize, cotton, soya beans), KnockOut® (for example maize), StarLink®(for example maize), Bollgard® (cotton), Nucotn® (cotton) and NewLeaf®(potato). Examples of herbicide-tolerant plants which may be mentionedare maize varieties, cotton varieties and soya bean varieties which aresold under the trade names Roundup Ready® (tolerance to glyphosate, forexample maize, cotton, soya bean), Liberty Link® (tolerance tophosphinotricin, for example oilseed rape), IMI® (tolerance toimidazolinones) and STS® (tolerance to sulphonylurea, for examplemaize). Herbicide-resistant plants (plants bred in a conventional mannerfor herbicide tolerance) which may be mentioned include the varietiessold under the name Clearfield® (for example maize). Of course, thesestatements also apply to cultivars having these genetic traits orgenetic traits still to be developed, which plants will be developedand/or marketed in the future.

[0642] The plants listed can be treated according to the invention in aparticularly advantageous manner with the compounds of the formula (I).The preferred ranges stated above for the active compounds also apply tothe treatment of these plants. Particular emphasis is given to thetreatment of plants with the mixtures specifically mentioned in thepresent text.

[0643] The active compounds can be converted into the customaryformulations such as solutions, emulsions, wettable powders,suspensions, powders, dusts, pastes, soluble powders, granules,suspension-emulsion concentrates, natural and synthetic materialsimpregnated with active compound, and microencapsulations in polymericmaterials.

[0644] These formulations are produced in a known manner, for example bymixing the active compounds with extenders, that is, liquid solventsand/or solid carriers, optionally with the use of surfactants, that is,emulsifiers and/or dispersants, and/or foam formers.

[0645] If the extender used is water, it is also possible, for example,to use organic solvents as cosolvents. The following are essentiallysuitable as liquid solvents: aromatics such as xylene, toluene oralkylnhaplhthalenies, chlorinated aromatics or chlorinated aliphatichydrocarbons such as chlorobenzenes, chloroethylenes or methylenechloride, aliphatic hydrocarbons such as cyclohexane or paraffins, forexample mineral oil fractions, mineral and vegetable oils, alcohols suchas butanol or glycol and their ethers and esters, ketones such asacetone, methyl ethyl ketone, methyl isobutyl ketone or cyclohexanone,strongly polar solvents such as dimethylformamide and dimethylsulphoxide, or else water.

[0646] Suitable solid carriers are: for example ammonium salts andground natural minerals such as kaolins, clays, talc, chalk, quartz,attapulgite, montmorillonite or diatomaceous earth, and ground syntheticmaterials such as highly-disperse silica, alumina and silicates;suitable solid carriers for granules are: for example crushed andfractionated natural rocks such as calcite, marble, pumice, sepioliteand dolomite, or else synthetic granules of inorganic and organic meals,and granules of organic material such as sawdust, coconut shells, maizecobs and tobacco stalks; suitable emulsifiers and/or foam formers are:for example nonionic and anionic emulsifiers such as polyoxyethylenefatty acid esters, polyoxyethylene fatty alcohol ethers, for examplealkylaryl polyglycol ethers, alkylsulphonates, alkyl sulphates,arylsulphonates, or else protein hydrolysates; suitable dispersants are:for example lignin-sulphite waste liquors and methylcellulose.

[0647] Tackifiers such as carboxymethylcellulose and natural andsynthetic polymers in the form of powders, granules or latices, such asgum arabic, polyvinyl alcohol and polyvinyl acetate, or else naturalphospholipids such as cephalins and lecithins and syntheticphospholipids can be used in the formulations. Other additives can bemineral and vegetable oils.

[0648] It is possible to use colorants such as inorganic pigments, forexample iron oxide, titanium oxide and Prussian Blue, and organiccolorants such alizarin colorants, azo colorants and metalphthalocyanine colorants, and trace nutrients such as salts of iron,manganese, boron, copper, cobalt, molybdenum and zinc.

[0649] The formulations generally comprise between 0.1 and 95%. byweight of active compound, preferably between 0.5 and 90%.

[0650] For controlling weeds, the active compounds according to theinvention, as such or in their formulations, can also be used asmixtures with known herbicides and/or substances which improve thecompatibility with crop plants (“safeners”), finished formulations ortank mixes being possible. Also possible are mixtures with weed-killerscomprising one or more known herbicides and a safener.

[0651] Possible components for the mixtures are known herbicides, forexample acetochlor, acifluorfen (-sodium), aclonifen, alachlor,alloxydim (-sodium), ametryne, amicarbazone, amidochlor, amidosulfuron,anilofos, asulam, atrazine, azafenidin, azimsulfuron, BAS-662H,beflubutamid, benazolin (-ethyl), benfuresate, bensulfuron (-methyl),bentazon, benzfendizone, benzobicyclon, benzofenap, benzoylprop(-ethyl), bialaphos, bifenox, bispyribac (-sodium), bromobutide,bromofenoxim, bromoxynil, butachlor, butafenacil (-allyl), butroxydim,butylate, cafenstrole, caloxydim, carbetamide, carfentrazone (-ethyl),chlomethoxyfen, chloramben, chloridazon, chlorimuron (-ethyl),chlornitrofen, chlorsulfuron, chloitoluron, cinidon (-ethyl),cinmethylin, cinosulfuron, clefoxydim, clethodim, clodinafop(-propargyl), clomazone, clomeprop, clopyralid, clopyrasulfuron(-methyl), cloransulam (-methyl), cumyluron, cyanazine, cybutryne,cycloate, cyclosulfamuron, cycloxydim, cyhalofop (-butyl), 2,4-D,2,4-DB, desmedipham, diallate, dicamba, dichlorprop (-P), diclofop(-methyl), diclosulam, diethatyl (-ethyl), difenzoquat, diflufenican,diflufenzopyr, dimefuron, dimepiperate, dimethachlor. dimnethametryn,dimethenamid, dimexyflam, dinitramine, diphenamid, diquat, dithiopyr,diuron, dymron, epropodan, EPTC, esprocarb, etlalfluralin,ethametsulfuron (-methyl), ethofumesate, ethoxyfen, ethoxysulfuron,etobenzamid, fenoxaprop (-P-ethyl), fentrazamide, flamprop (-isopropyl,-isopropyl-L, -methyl), flazasulfuron, florasulam, fluazifop (-P-butyl),fluazolate, flucarbazone (-sodium), flufenacet, flumetsulam, flumiclorac(-pentyl), flumioxazin, flumipropyn, flumetsulam, fluometuron,fluorochloridone, fluoroglycofen (-ethyl), flupoxam, flupropacil,flurpyrsulfuron (-methyl, -sodium), flurenol (-butyl), fluridone,fluroxypyr (-butoxypropyl, -meptyl), flurprimidol, flurtamone,fluthiacet (-methyl), fluthiamide, fomesafen, foramsulfuron, glufosinate(-ammonium), glyphosate (-isopropylammonium), halosafen, haloxyfop(-ethoxyethyl, -P-methyl), hexazinone, imazamethabenz (-methyl),imazamethapyr, imazamox, imazapic, imazapyr, imazaquin, imazethapyr,imazosulfuron, iodosulfuron (-methyl, -sodium), ioxynil, isopropalin,isoproturon, isouron, isoxaben, isoxachlortole, isoxaflutole,isoxapyrifop, lactofen, lenacil, linuron, MCPA, mecoprop, mefenacet,mesotrione, metamitron, metazachlor, methabenzthiazuron, metobenzuron,metobromuron, (alpha-) metolachlor, metosulam, metoxuron, metribuzin,metsulfuron (-methyl), molinate, monolinuron, naproanilide, naproparide,neburon, nicosulfuron, norflurazon, orbencarb, oryzalin, oxadiargyl,oxadiazon, oxasulfuron, oxaziclomefone, oxyfluorfen, paraquat,pelargonic acid, pendimethalin, pendralin, pentoxazone, phenmedipham,picolinafen, piperophos, pretilachlor, primisulfuron (-methyl),profluazol, prometryn, propachlor, propanil, propaquizafop,propisochlor, propoxycarbazone (-sodium), propyzamide, prosulfocarb,prosulfuron, pyraflufen (-ethyl), pyrazogyl, pyrazolate, pyrazosulfuron(-ethyl), pyrazoxyfen, pyribenzoxim, pyributicarb, pyridate, pyridatol,pyriftalid, pyriminobac (-methyl), pyrithiobac (-sodium), quinchlorac,quinmerac, quinoclamine, quizalofop(-P-ethyl, -P-tefuryl), rimsulfuron,sethoxydim, simazine, simetryn, sulcotrione, sulfentrazone, sulfometuron(-methyl), sulfosate, sulfosulfuron, tebutam, tebuthiuron, tepraloxydim,terbuthylazine, terbutryn, thenylchlor, thiafluamide, thiazopyr,thidiazimin, thifensulfuron (-methyl), thiobencarb, tiocarbazil,tralkoxydim, triallate, triasulfuron, tribenuron (-methyl), triclopyr,tridiphane, trifluralin, trifloxysulfuron, triflusulfuron (-methyl),tritosulfuron.

[0652] A mixture with other known active compounds, such as fungicides,insecticides, acaricides, nematicides, bird repellents, plant nutrientsand agents which improve soil structure, is also possible.

[0653] The active compounds can be used as such, in the form of theirformulations or in the use forms prepared therefrom by further dilution,such as ready-to-use solutions, suspensions, emulsions, powders, pastesand granules. They are used in a customary manner, for example bywatering, spraying, atomizing or broadcasting.

[0654] The active compounds according to the invention can be appliedboth before and after emergence of the plants. They can also beincorporated into the soil before sowing.

[0655] The amount of active compound used can vary within a relativelywide range. It depends essentially on the nature of the desired effect.In general, the amounts used are between 1 g and 10 kg of activecompound per hectare of soil surface, preferably between 5 g and 5 kgper ha.

[0656] The preparation and the use of the active compounds according tothe invention is 5 illustrated by the examples below.

Preparation Examples EXAMPLE I-a-1

[0657]

[0658] 5.6 g (50 mmol) of potassium tert-butoxide are initially chargedin 30 ml of absolute DMF and, at 60° C., admixed with 10.6 g of thecompound according to Example II-8 in 20 ml of DMF. The reactionsolution is stirred at 60° C. for 3 hours, poured into ice-water andacidified with concentrated hydrochloric acid. The precipitate isfiltered off with suction, washed and dried.

[0659] Yield: 7.4 g (77% of theory), m.p. >220° C.

EXAMPLE I-a-2

[0660]

[0661] 9.8 g (44 mmol) of 2,4,5-trimethylphenyl chlorocarbonyl keteneare initially charged in 80 ml of anhydrous xylene and, at 20° C., 8.1 g(44 mmol) of trimethylsityloxy-methylidenecyclohexane in 30 ml ofanhydrous xylene are added dropwise with exclusion of moisture. Themixture is heated at reflux for 8 hours, 7.3 ml of methanol are thenadded, and heating at reflux is continued for another 2 hours. Themixture is washed with water and saturated sodium chloride solution anddried over sodium sulphate. The mixture is concentrated under reducedpressure and the residue is chromatographed on silica gel (35 to 70 μm)using toluene/acetone (20:1).

[0662] Yield: 3.9 g ({circumflex over ( )} 27% of theory). m.p. 174-175°C.

EXAMPLE I-a-3

[0663]

[0664] 9.4 g (42.2 mmol) of 2,4,5-trimethylphenyl chlorocarbonyl keteneare initially charged in 80 ml of anhydrous xylene and, at 20° C., 7.1 g(42.2 mmol) of trimethylsilyloxymethylidenecyclopentane in 30 ml ofanhydrous xylene are added dropwise with exclusion of moisture. Themixture is heated at reflux for 8 hours and then washed with water andsaturated sodium chloride solution, and the organic phase is dried oversodium sulphate. The organic phase is evaporated and the residue ischromatographed on silica gel (35 to 70 μm) using the mobile phasetoluene.

[0665] Yield: 3.2 g ({circumflex over ( )} 25% of theory). m.p. 122-124°C.

[0666] The following compounds of the formula I-a are obtainedanalogously to Examples I-a-1, I-a-2 and I-a-3 and in accordance withthe general statements on the preparation (I-a)

Ex. No. W X Y Z B A Q¹ Q² m.p. ° C. I-a-4 H CH₃ 4-Cl H CH₃ CH₃ OCH₃ H164-166 I-a-5 H CH₃ 5-(4-Cl—C₆H₄) H CH₃ CH₃ H H wax I-a-6 H CH₃5-(4-Cl—C₆H₄) H CH₃ CH₃ CH₃ CH₃ 125 I-a-7 CH₃ CH₃ 4-CH₃ H CH₃ CH₃ CH₃CH₃ 140 I-a-8 H CH₃ 5-CH₃ H CH₃ CH₃ OCH₃ H oil I-a-9 CH₃ CH₃ 3-CH₃ 4-CH₃CH₃ CH₃ OCH₃ H 121-122 I-a-10 CH₃ CH₃ 3-CH₃ 4-CH₃ CH₃ CH₃ OH H 184-186I-a-11 CH₃ CH₃ 4-CH₃ H CH₃ CH₃ OCH₃ H 115-117 I-a-12 CH₃ CH₃ 4-CH₃ H

H 171 I-a-13 CH₃ CH₃ 4-(4-Cl—C₆H₄) H CH₃ CH₃ H H 174 I-a-14 CH₃ CH₃4-CH₃ H CH₃ CH₃ OC₂H₅ H 90-93 I-a-15 CH₃ CH₃ 4-CH₃ H —(CH₂)₅— OC₂H₅ H148-150 I-a-16 CH₃ CH₃ 4-CH₃ H CH₃ CH₃ OC₃H₇ H 108-110 I-a-17 CH₃ CH₃4-CH₃ H CH₃ C₂H₅ OCH₃ H 111-113 I-a-18 CH₃ CH₃ 4-CH₃ H C₂H₅ C₂H₅ OCH₃ H123-125 I-a-19 CH₃ CH₃ 4-CH₃ H —(CH₂)₅— OH H 154-156 I-a-20 H CH₃5-(3-Cl—C₆H₄) H CH₃ CH₃ CH₃ CH₃ oil I-a-21 H CH₃ 5-(4-Cl—C₆H₄₎ 4-CH₃ CH₃CH₃ CH₃ CH₃ 182-184° C. I-a-22 CH₃ CH₃ 5-(4-Cl—C₆H₄₎ 4-CH₃ CH₃ CH₃ CH₃CH₃ 233-234° C. I-a-23 H CH₃ 5-Br H CH₃ CH₃ CH₃ CH₃ 184-186° C. I-a-24 HCH₃ 5-(3,5-Cl₂—C₆H₃) H CH₃ CH₃ CH₃ CH₃ 192-193° C. I-a-25 H CH₃5-(2-CH₃, 4-Cl— H CH₃ CH₃ CH₃ CH₃ 202-203° C. C₆H₃) I-a-26 H CF₃ 4-Cl HCH₃ CH₃ CH₃ CH₃ 185-186° C. I-a-27 Br C₃H₇ 4-Br H CH₃ CH₃ CH₃ CH₃ oilI-a-28 C₂H₅ C₂H₅ 4-Br H CH₃ CH₃ CH₃ CH₃ 178-180° C. I-a-29 Cl Cl 4-CF₃ HCH₃ CH₃ CH₃ CH₃ 233-234° C. I-a-30 Cl Cl 4-Cl H CH₃ CH₃ CH₃ CH₃ >250° C.I-a-31 H Cl 5-(4-Cl—C₆H₄₎ H CH₃ CH₃ CH₃ CH₃ 204-205° C.

EXAMPLE I-A-b-1

[0667]

[0668] 1.5 g (3.9 mmol) of the compound according to Example I-a-1 areinitially charged in 15 ml of anhydrous dichloromethane and admixed with0.78 ml (5.85 mmol) of triethylamine. At 0° C., 0.57 g (5.07 mmol) ofisobutyryl chloride are added, and the mixture is stilled at roomtemperature for 2 hours. The reaction solution is extracted with 10%strength citric acid and washed with dichloromethane. The mixture isthen extracted with 1 N NaOH and washed once more with dichloromethaneand dried, and the solvent is evaporated.

[0669] Yield: 1.2 g ({circumflex over ( )} 68% of theory). ¹H-NMR (400MHz, DMSO): δ=0.69 (d, 6H, (CH ₃)₂—CH); 1.17 (s, 6H, (CH₃)₂—C), 1.52 (s,6H, (CH₃)₂—C—O), 2.11 (s, 6H, 2 Ar—CH₃) ppm.

[0670] The following compounds of the formulae (I-A-b) and (I-B-b) areobtained analogously to Examples (I-A-b-1) and in accordance with thegeneral statements on the preparation (I-A-b)

(I-B-b)

Ex. No. W X Y Z B A Q¹ Q² R¹ m.p. ° C. I-A-b-2 H CH₃ 5-CH₃ H CH₃ CH₃OCH₃ H CH₃ oil I-A-b-3 H CH₃ 4-Cl H CH₃ CH₃ OCH₃ H CH₃ oil I-A-b-4 CH₃CH₃ 4-CH₃ H

H CH(CH₃)₂ 84-86 I-A-b-5 CH₃ CH₃ 4-CH₃ H CH₃ CH₃ OCH₃ H CH₃ 118-120I-A-b-6 CH₃ CH₃ 4-CH₃ H CH₃ CH₃ OCH₃ H

115-117 I-A-b-7 CH₃ CH₃ 4-CH₃ H CH₃ CH₃ OCH₃ H

oil I-A-b-8 CH₃ CH₃ 4-CH₃ H CH₃ CH₃ O—COCH₃ H CH₃ 125-127 I-A-b-9 CH₃CH₃ 4-CH₃ H —(CH₂)₄— O—COCH₃ H CH₃ 122-124 I-A-b-10 H CH₃ 5-(4-Cl—C₆H₄)H CH₃ CH₃ CH₃ CH₃ i-C₃H₇ oil I-A-b-11 CH₃ CH₃ 4-(4-Cl—C₆H₄) H CH₃ CH₃ HH i-C₃H₇ oil I-B-b-12 H CH₃ 5-CH₃ H CH₃ H₃ OCH₃ H CH₃ oil I-B-b-13 H CH₃4-Cl H CH₃ H₃ OCH₃ H CH₃ oil I-B-b-14 CH₃ CH₃ 4-CH₃ H CH₃ CH₃ OCH₃ H CH₃110-113 I-B-b-15 CH₃ CH₃ 4-CH₃ H CH₃ CH₃ OCH₃ H

134-136 I-B-b-16 CH₃ CH₃ 4-CH₃ H CH₃ CH₃ CH₃ CH₃ i-C₃H₇ oil I-B-b-17 CH₃CH₃ 4-CH₃ H CH₃ CH₃ H H i-C₃H₇ 88-91 I-A-b-18 H CH₃ 5-(4-Cl—C₆H₄) H CH₃CH₃ H H i-C₃H₇ oil

[0671] Isomer mixtures of the formulae I-A-b and I-B-b were separated bysilica gel column chromatography.

EXAMPLE I-A-c-1

[0672]

[0673] 1.5 g (3.9 mmol) of the compound according to Example I-a-1 areinitially charged in 15 ml of anhydrous dichloromethane and admixed with0.78 ml (5.85 mmol) of triethylamine. At 0° C., 0.63 g (5.07 mmol) ofisopropyl chloroformate are added, and the mixture is stirred at roomtemperature for 2 hours. The reaction solution is extracted with 10%strength citric acid and washed with dichlorometlhane. The mixture isthen extracted with 1 N NaOH and washed once more with dichloromethaneand dried, and the solvent is evaporated.

[0674] Yield: 1.2 g ({circumflex over ( )} 65% of theory). ¹H-NMR (400MHz, DMSO): δ=1.08 (d, 6H, (CH ₃)₂—CH); 1.16 (s, 6H, (CH₃)₂—C), 2.11 (s,6H, 2 Ar—CH₃), 7.36 (s, 2H, 2 Ar—H) ppm.

[0675] The following compounds of the formulae (I-A-c) and (I-B-c) wereobtained analogously to Example I-A-c-1 and in accordance with thegeneral statements on the preparation (I-A-c)

(I-B-c)

Ex. No. W X Y Z B A Q¹ Q² M R² m.p. ° C. I-A-c-2 CH₃ CH₃ 4-CH₃ H CH₃ CH₃OCH₃ H O CH₃ 108-110 I-A-c-3 H CH₃ 5-(4-Cl—C₆H₄) H CH₃ CH₃ CH₃ CH₃ Oi-C₃H₇ oil I-A-c-4 CH₃ CH₃ 4-(4-Cl—C₆H₄) H CH₃ CH₃ H H O i-C₃H₇ oilI-B-c-1 CH₃ CH₃ 4-CH₃ H CH₃ CH₃ H H O i-C₃H₇ oil I-B-c-2 CH₃ CH₃ 4-CH₃ H

H O i-C₃H₇ oil I-B-c-7 CH₃ CH₃ 4-CH₃ H CH₃ CH₃ H H O i-C₃H₇ oil I-A-c-8H CH₃ 5-(4-Cl—C₆H₄) H CH₃ CH₃ H H O C₂H₅ oil I-A-c-9 H CH₃ 5-(4-Cl—C₆H₄)H CH₃ CH₃ CH₃ CH₃ O C₂H₅ 144 I-A-c-10 H CH₃ 5-(4-Cl—C₆H₄) 4-CH₃ CH₃ CH₃CH₃ CH₃ O C₂H₅ oil I-A-c-11 H CH₃ 5-(3-Cl—C₆H₄) H CH₃ CH₃ CH₃ CH₃ O C₂H₅I-A-c-12 H CH₃ 5-Br H CH₃ CH₃ CH₃ CH₃ O C₂H₅ oil

EXAMPLE II-1

[0676]

[0677] Preparation of the Acyl Chloride:

[0678] 9.0 g (34.5 mmol) of 2-methyl-5-(4-chlorophenyl)-phenylaceticacid are initially charged in 50 ml of anhydrous toluene and 2 drops ofDMF, and 6.15 g (51.8 mmol; 3.74 ml) of thionyl chloride are added. Themixture is stirred at 100° C. until evolution of gas has ceased. Thesolvent is distilled off.

[0679] 6.00 g (34.5 mmol) of ethyl 3-hydroxy-2,2,3-trimethyl-butyrateand 10.3 g (34.5 mmol) of acyl chloride in 40 ml of anhydrous tolueneare boiled at reflux overnight. The solvent is then distilled off andthe reaction mixture is purified by silica gel column chromatography(petroleum ether:ethyl acetate. 3:11:1).

[0680] Yield: 11.6 g ({circumflex over ( )} 80.6% of theory). ¹H-NMR(DMSO, 400 MHz): δ=1.06 (s, 6H, 2CH₃), 1.12 (t, 3H, CO₂CH₂CH ₃), 1.50(s, 6H, 2CH₃), 2.26 (s, 3H, Ar—CH₃), 3.66 (s, 2H, CH₂), 4.00 (q, 2H,CO₂CH ₂CH₃) ppm.

[0681] The following compounds of the formula (II) are obtainedanalogously to Example II-1 and in accordance with the generalstatements on the preparation (II)

Ex. No. W X Y Z B A Q¹ Q² R⁸ m.p. ° C. II-2 CH₃ CH₃ 4-CH₃ H

H C₂H₅ oil II-3 CH₃ CH₃ 4-CH₃ H CH₃ CH₃ CH₃ CH₃ C₂H₅ oil II-4 CH₃ CH₃4-CH₃ H CH₃ CH₃ H H CH₃ oil II-5 H CH₃ 5-(4-Cl—C₆H₄) H CH₃ CH₃ H H CH₃oil II-6 H CH₃ 5-(4-Cl—C₆H₄) H CH₃ CH₃ CH₃ CH₃ C₂H₅ oil II-7 CH₃ CH₃4-(4-Cl—C₆H₄) H CH₃ CH₃ H H CH₃ oil II-8 CH₃ CH₃ 4-(4-Cl—C₆H₄) H CH₃ CH₃CH₃ CH₃ C₂H₅ oil II-9 H CH₃ 5-(3-Cl—C₆H₄) H CH₃ CH₃ CH₃ CH₃ C₂H₅ oilII-10 H CH₃ 5-(4-Cl—C₆H₄) 4-CH₃ CH₃ CH₃ CH₃ CH₃ C₂H₅ oil II-11 CH₃ CH₃5-(4-Cl—C₆H₄) 4-CH₃ CH₃ CH₃ CH₃ CH₃ C₂H₅ oil II-12 H CH₃ 5-Br H CH₃ CH₃CH₃ CH₃ C₂H₅ oil II-13 H CH₃ 5-(3,5-Cl₂— H CH₃ CH₃ CH₃ CH₃ C₂H₅ oilC₆H₃) II-14 H CF₃ 4-Cl H CH₃ CH₃ CH₃ CH₃ C₂H₅ oil II-15 Br C₃H₇ 4-Br HCH₃ CH₃ CH₃ CH₃ C₂H₅ oil II-16 C₂H₅ C₂H₅ 4-Br H CH₃ CH₃ CH₃ CH₃ C₂H₅ oilII-17 Cl Cl 4-CF₃ H CH₃ CH₃ CH₃ CH₃ C₂H₅ oil II-18 Cl Cl 4-Cl H CH₃ CH₃CH₃ CH₃ C₂H₅ oil II-19 H Cl 5-(4-Cl—C₆H₄) H CH₃ CH₃ CH₃ CH₃ C₂H₅ oil

[0682] The compounds were obtained as oils and used without furtherpurification for preparing compounds of the formula (I-a).

Use Examples EXAMPLE A

[0683] Meloidogyne Test

[0684] Solvent: 30 parts by weight of dimethylformamide

[0685] Emulsifier: 1 part by weight of alkylaryl polyglycol ether

[0686] To produce a suitable preparation of active compound, 1 part byweight of active compound is mixed with the stated amounts of solventand emulsifier, and the concentrate is diluted with water to the desiredconcentration.

[0687] Containers are filled with sand, solution of active compound,Meloidogyne incognita egg/larvae suspension and lettuce seeds. Thelettuce seeds germinate and the plants develop. On the roots, galls areformed.

[0688] After the desired period of time, the nematicidal action in % isdetermined using the formation of galls as a measure. 100% means that nogalls have been found; 0% means that the number of galls on the treatedplants corresponds to that on the untreated control.

[0689] In this test, for example, the following compounds of thePreparation Examples exhibit good activity.

[0690] Table A

[0691] Plant-Damaging Nematodes

[0692] Meloidogyne Test Active compound Kill rate in % after Activecompounds concentration in ppm 14^(d) Ex. I-a-5 20 100 Ex. I-B-b-17 2090 Ex. I-B-c-1 20 90 Ex. I-A-b-4 20 90 Ex. I-B-c-2 20 100 Ex. I-A-b-1020 100 Ex. I-A-b-1 20 100

EXAMPLE B

[0693] Myzus Test

[0694] Solvent: 30 parts by weight of dimethylformamide

[0695] Emulsifier: 1 part by weight of alkylaryl polyglycol ether

[0696] To produce a suitable preparation of active compound, 1 part byweight of active compound is mixed with the stated amounts of solventand emulsifier, and the concentrate is diluted with water to the desiredconcentration.

[0697] Cabbage leaves (Brassica oleracea) which are heavily infested bythe peach aphid (Myzus persicae) are treated by being dipped into apreparation of active compound of the desired concentration.

[0698] After the desired period of time, the kill in % is determined.100% means that all of the aphids have been killed: 0% means that noneof the aphids has been killed.

[0699] In this test, for example, the following compounds of thePreparation Examples show good activity.

[0700] Table B

[0701] Plant-Damaging Insects

[0702] Myzus Test Active compound Kill rate in % after Active compoundsconcentration in ppm 6^(d) Ex. I-a-5 1000 95 Ex. I-a-7 1000 90 Ex. I-a-61000 95

EXAMPLE C

[0703] Panonychus Test

[0704] Solvent: 3 parts by weight of dimethylformamide

[0705] Emulsifier: 1 part by weight of alkylaryl polyglycol ether

[0706] To produce a suitable preparation of active compound, 1 part byweight of active compound is mixed with the stated amounts of solventand emulsifier, and the concentrate is diluted with water to the desiredconcentration.

[0707] Plum trees (Prunus domestica), of a height of approximately 30cm, which are heavily infested by all stages of the fruit tree redspider mite (Panonychus ulmi) are sprayed with a preparation of activecompound of the desired concentration.

[0708] After the desired period of time, the effect in % is determined.100% means that all of the spider mites have been killed: 0% means thatnone of the spider mites has been killed.

[0709] In this test, for example, the following compound of thePreparation Examples shows good activity.

[0710] Table C

[0711] Plant-Damaging Mites

[0712] Panonychus Test Active compound Kill rate in % after Activecompounds concentration in ppm 14^(d) Ex. I-a-6 200 100

EXAMPLE D

[0713]Phaedon larvae Test

[0714] Solvent: 30 parts by weight of dimethylformamide

[0715] Emulsifier: 1 part by weight of alkylaryl polyglycol ether

[0716] To produce a suitable preparation of active compound, 1 part byweight of active compound is mixed with the stated amounts of solventand emulsifier, and the concentrate is diluted with water to the desiredconcentration.

[0717] Cabbage leaves (Brassica oleracea) are treated by being dippedinto the preparation of active compound of the desired concentration andare populated with larvae of the mustard beetle (Phaedon cochleariae)while the leaves are still moist.

[0718] After the desired period of time, the kill in % is determined.100% means that all of the beetle larvae have been killed. 0% means thatnone of the beetle larvae has been killed.

[0719] In this test, for example, the following compounds of thePreparation Examples show good activity.

[0720] Table D

[0721] Plant-Damaging Insects

[0722]Phaedon larvae Test Active compound Kill rate in % after Activecompounds concentration in ppm 7^(d) Ex. I-a-5 1000 100 Ex. I-a-6 1000100 Ex. I-A-b-10 1000 100 Ex. I-A-c-3 1000 90 Ex. I-a-13 1000 100 Ex.I-a-1 1000 100 Ex. I-A-b-11 1000 100

EXAMPLE E

[0723]Spodoptera frugiperda Test

[0724] Solvent: 30 parts by weight of dimethylformamide

[0725] Emulsifier: 1 part by weight of alkylaryl polyglycol ether

[0726] To produce a suitable preparation of active compound, 1 part byweight of active compound is mixed with the stated amounts of solventand emulsifier, and the concentrate is diluted with water to the desiredconcentration.

[0727] Cabbage leaves (Brassica oleracea) are treated by being dippedinto the preparation of active compound of the desired concentration andare populated with caterpillars of the army worm (Spodoptera frugiperda)while the leaves are still moist.

[0728] After the desired period of time, the kill in % is determined.100% means that all of the caterpillars have been killed; 0%. means thatnone of the caterpillars has been killed.

[0729] In this test, for example, the following compounds of thePreparation Examples show good activity.

[0730] Table E

[0731] Plant-Damaging Insects

[0732]Spodoptera frugiperda Test Active compound Kill rate in % afterActive compounds concentration in ppm 7^(d) Ex. I-a-6 1000 100 Ex.I-A-b-10 1000 100

EXAMPLE F

[0733] Tetranychus Test (OP-Resistant/Dip Treatment)

[0734] Solvent: 30 parts by weight of dimethylformamide

[0735] Emulsifier: 1 part by weight of alkylaryl polyglycol ether

[0736] To produce a suitable preparation of active compound, 1 part byweight of active compound is mixed with the stated amounts of solventand emulsifier, and the concentrate is diluted with water to the desiredconcentration.

[0737] Bean plants (Phaseolus vulgaris) which are heavily infested byall stages of the greenhouse red spider mite (Tetranychus urticae) aredipped into a preparation of active compound of the desiredconcentration.

[0738] After the desired period of time, the effect in % is determined.100% means that all of the spider mites have been killed, 0% means thatnone of the spider mites has been killed.

[0739] In this test, for example, the following compounds of thePreparation Examples show an activity which is superior to the priorart.

[0740] In this test, for example, the following compounds of thePreparation Examples show good activity.

[0741] Table F

[0742] Plant-Damaging Mites

[0743] Tetranychus Test (OP-Resistant/Dip Treatment) Active compoundKill rate in % after Active compounds concentration in ppm 7^(d) Ex.I-a-6 100 100 Ex. I-B-b-17 100 100 Ex. I-B-c-1 100 100 Ex. I-B-c-2 10099 Ex. I-B-b-16 100 100 Ex. I-A-c-3 0.01 100

EXAMPLE G

[0744] Meloidogyne Test

[0745] Solvent: 8 parts by weight of dimethylformamide

[0746] Emulsifier: 1 part by weight of alkylaryl polyglycol ether

[0747] To produce a suitable preparation of active compound, 1 part byweight of active compound is mixed with the stated amounts of solventand emulsifier, and the concentrate is diluted with water to the desiredconcentration.

[0748] Containers are filled with sand, solution of active compound.Meloidogyne incognita egg/larvae suspension and lettuce seeds. Thelettuce seeds germinate and the plants develop. On the roots, galls areformed.

[0749] After the desired period of time, the nematicidal action in % isdetermined usinIg the formation of galls as a measure. 100% means thatno galls have been found; 0% means that the number of galls on thetreated plants corresponds to that on the untreated control.

[0750] Active compounds, application rates and results are shown in thetable below:

[0751] Table G

[0752] Nematicides

[0753]Meloidogyne incognita Kill rate in % at active Active compoundcompound concentration in ppm Ex. I-a-7 20 ppm = 100%

EXAMPLE H

[0754] Sphaerotheca Test (Cucumber)/Protective

[0755] Solvent: 48.8 parts by weight of N,N-dimethylformamide

[0756] Emulsifier: 1.2 parts by weight of alkylaryl polyglycol ether

[0757] To produce a suitable preparation of active compound, 1 part byweight of active compound is mixed with the stated amounts of solventand emulsifier, and the concentrate is diluted with water to the desiredconcentration.

[0758] To test for protective activity, young cucumber plants aresprayed with the preparation of active compound at the statedapplication rate. 1 day after the treatment, the plants are inoculatedwith a spore suspension of Sphaerotheca fuliginea. The plants are thenplaced in a greenhouse at 70% relative atmospheric humidity and atemperature of 23° C.

[0759] Evaluation is carried out 7 days after the inoculation. 0% meansan efficacy which corresponds to that of the control, whereas anefficacy of 100% meais that no infection is observed.

[0760] Table H

[0761] Sphaerotheca Test (Cucumber)/Protective Application rate ofactive compound Active compound in g/ha Efficacy in % Ex. I-B-b-13 75070 Ex. I-A-b-3 750 80

EXAMPLE I

[0762] Critical Concentration Test/Soil Insects—Treatment of TransgenicPlants Test insect: Diabrotica balteata - larvae in soil Solvent: 7parts by weight of acetone Emulsifier: 1 part by weight of alkylarylpolyglycol ether

[0763] To produce a suitable preparation of active compound, 1 part byweight of active compound is mixed with the stated amount of solvent,the stated amount of emulsifier is added and the concentrate is dilutedwith water to the desired concentration.

[0764] The preparation of active compound is poured onto the soil. Here,the concentration of active compound in the preparation is virtuallyirrelevant, only the amount by weight of active compound per volume unitof soil, which is stated in ppm (mg/l), matters. The soil is filled into0.25 l pots and these are allowed to stand at 20° C.

[0765] Immediately after preparation, 5 pre-germinated maize corns ofthe variety YIELD GUARD (trademark of Monsanto Comp., USA) are placedinto each pot. After 2 days, the test insects in question are placedinto the treated soil. After a further 7 days, the efficacy of theactive compound is determined by counting the maize plants that haveemerged (1 plant=20% efficacy).

EXAMPLE J

[0766]Heliothis virescens Test—Treatment of Transgenic Plants Solvent: 7parts by weight of acetone Emulsifier: 1 part by weight of alkylarylpolyglycol ether

[0767] To produce a suitable preparation of active compound, 1 part byweight of active compound is mixed with the stated amount of solvent andthe stated amount of emulsifier, and the concentrate is diluted withwater to the desired concentration.

[0768] Soybean shoots (Glycine max) of the variety Roundup Ready(tradename of Monsanto Comp. USA) are treated by being dipped into thepreparation of active compound of the desired concentration and arepopulated with the tobacco budworm Heliothis virescens while the leavesare still moist.

[0769] After the desired period of time, the kill of the insects isdetermined.

1. Compounds of the formula (I)

in which W represents hydrogen, alkyl, alkenyl, alkinyl, halogen,halogenoalkyl or alkoxy, X represents halogen, alkyl, alkoxy, alkenyl,alkinyl, halogenoalkyl, halogenoalkoxy, cyano or in each case optionallysubstituted phenyl, phenoxy, phenylthio, phenylalkoxy orphenylalkylthio. Y represents hydrogen, alkyl, hydrogen, halogenoalkyl,alkoxy, alkenyl, alkinyl or optionally substituted aryl or hetaryl, Zrepresents hydrogen, halogen, alkyl, alkoxy, halogenoalkyl,halogenoalkoxy or cyano, A represents a bond, hydrogen, in each caseoptionally halogen-substituted alkyl, alkenyl, alkoxyalkyl, optionallysubstituted cycloalkyl or cycloalkylalkyl in which optionally at leastone ring atom is replaced by a hetero atom, or in each case optionallyhalogen-, alkyl-, halogenoalkyl-, alkoxy-, halogenoalkoxy-, cyano- ornitro-substituted aryl, arylalkyl, hetaryl or hetarylalkyl, B representshydrogen or alkyl, or A and B together with the carbon atom to whichthey are attached represent a saturated or unsaturated unsubstituted orsubstituted cycle which optionally contains at least one hetero atom, orB and Q¹ together represent alkanediyl which is optionally substitutedby in each case optionally substituted alkyl or alkoxy and in which twonot directly adjacent carbon atoms optionally form a further optionallysubstituted cycle or Q¹ represents hydrogen, hydroxyl, alkyl, alkoxy,alkoxyalkyl, alkylacyloxy, optionally substituted cycloalkyl (in whichoptionally one methylene group is replaced by oxygen or sulphur) oroptionally substituted phenyl, Q² represents hydrogen or alkyl, or Q¹and Q² together with the carbon atom to which they are attachedrepresent an unsubstituted or substituted cycle which optionallycontains a hetero atom, G represents hydrogen (a) or represents one ofthe groups

in which E represents a metal ion or an ammonium ion, L representsoxygen or sulphur, M represents oxygen or sulphur, R¹ represents in eachcase optionally halogen-substituted alkyl, alkenyl, alkoxyalkyl,alkylthioalkyl, polyalkoxyalkyl or optionally halogen-, alkyl- oralkoxy-substituted cycloalkyl in which one or more methylene groups maybe replaced by hetero atoms, in each case optionally substituted phenyl,phenylalkyl, hetaryl, phenoxyalkyl or hetaryloxyalkyl, R² represents ineach case optionally halogen-substituted alkyl alkenyl, alkoxyalkyl,polyalkoxyalkyl or represents in each case optionally substitutedcycloalkyl, phenyl or benzyl, R³, R⁴ and R⁵ independently of one anothereach represent in each case optionally halogen-substituted alkyl,alkoxy, alkylamino, dialkylamino, alkylthio, alkenylthio,cycloalkylthilo and represent in each case optionally substitutedphenyl, benzyl, phenoxy or phenylthio, and R⁶ and R⁷ independently ofone another each represent hydrogen, in each case optionallyhalogen-substituted alkyl, cycloalkyl, alkenyl, alkoxy, alkoxyalkyl,represent optionally substituted phenyl, represent optionallysubstituted benzyl, or together with the N atom to which they areattached represent a ring which is optionally interrupted by oxygen orsulphur.
 2. Compounds of the formula (I) according to claim 1 in which Wrepresents hydrogen, C₁-C₆-alkyl, C₂-C₄-alkenyl, ethinyl, fluorine,chlorine, bromine, C₁-C₄-halogenoalkyl or C₁-C₆-alkoxy, X representsfluorine, chlorine, bromine, C₁-C₆-alkyl, C₁-C₄-halogenoalkyl,C₁-C₆-alkoxy, C₂-C₄-alkenyl, ethinyl, C₁-C₄-halo-genoalkoxy, cyano or ineach case optionally halogen-, C₁-C₆-alkyl-, C₁-C₆-alkoxy-,C₁-C₄-halogenoalkyl-, C₁-C₄-halogenoalkoxy-, nitro- or cyano-substitutedphenyl or benzyloxy, Y represents hydrogen, C₁-C₆-alkyl,C₁-C₄-halogenoalkyl, fluorine, chlorine, bromine, C₁-C₆-alkoxy,C₂-C₄-alkenyl, ethinyl or represents one of the radicals

V¹ represents hydrogen, halogen, C₁-C₁₂-alkyl, C₁-C₆-alkoxy,C₁-C₆-alkylthio, C₁-C₄-halogenoalkyl, C₁-C₄-halogenoalkoxy, nitro, cyanoor represents phenyl, phenoxy, phenoxy-C₁-C₄-alkyl, phenyl-C₁-C₄-alkoxy,phenylthio-C₁-C₄-alkyl or phenyl-C₁-C₄-alkylthio, each of which isoptionally mono- or polysubstituted by halogen, C₁-C₆-alkyl,C₁-C₆-alkoxy, C₁-C₄-halogenoalkyl, C₁-C₄-halogenoalkoxy, nitro or cyano,V² represents hydrogen, fluorine, chlorine, C₁-C₆-alkyl, C₁-C₆-alkoxy,C₁-C₄-halogenoalkyl or C₁-C₄-halogenoalkoxy, V³ represents hydrogen,fluorine, chlorine, methyl or methoxy, Z represents hydrogen, fluorine,chlorine, bromine, C₁-C₆-alkyl, C₁-C₄-halogenoalkyl, C₁-C₆-alkoxy,C₁-C₄-halogenoalkoxy or cyano, with the first proviso, that W, X and Zdo not represent bromine, C₂-C₄-alkenyl and ethinyl if Y represents V¹-,V²- and V³-substituted phenyl or hetaryl and that secondly only at mosttwo of the radicals W, X and Y represent C₂-C₄-alkenyl or ethinyl, withthe proviso that none of the other radicals W, X, Y and Z may representbromine, A represents a bond, hydrogen or in each case optionallyhalogen-substituted C₁-C₁₂-alkyl, C₃-C₈-alkenyl,C₁-C₆-alkoxy-C₁-C₄-alkyl, in each case optionally halogen-, C₁-C₄-alkyl-or C₁-C₄-alkoxy-substituted C₃-C₈-cycloalkyl orC₃-C₆-cycloalkyl-C₁-C₄-alkyl in which optionally one or two not directlyadjacent ring members are replaced by oxygen and/or sulphur orrepresents in each case optionally halogen-, C₁-C₆-alkyl-,C₁-C₆-halogenoalkyl-, C₁-C₆-alkoxy, C₁-C₆-halogenoalkoxy-, cyano- ornitro-substituted phenyl, benzyl, hetaryl having 5 or 6 ring atoms orhetaryl-C₁-C₄-alkyl having 5 or 6 ring atoms, B represents hydrogen orC₁-C₆-alkyl, or A, B and the carbon atom to which they are attachedrepresent saturated C₃-C₁₀-cycloalkyl or unsaturated C₅-C₁₀-cycloalkylin which optionally one ring member is replaced by oxygen or sulphur andwhich are optionally mono- or disubstituted by C₁-C₆-alkyl,C₃-C₈-cycloalkyl, C₁-C₆-halogenoalkyl, C₁-C₆-alkoxy, C₁-C₆-alkylthio,halogen or phenyl, with the proviso that Q¹ and Q² do not form a furthercycle, or B and Q¹ together represent C₃-C₆-alkanediyl which isoptionally mono- or disubstituted by identical or different C₁-C₄-alkyland in which two not directly adjacent carbon atoms optionally form afurther 3- to 6-membered cycle, or Q¹ represents hydrogen, hydroxyl,C₁-C₆-alkyl, C₁-C₆-alkoxy, C₁-C₆-alkoxy-C₁-C₂-alkyl, C₁-C₆-alkylacyloxy,optionally fluorine-, chlorine-, C₁-C₄-alkyl-, C₁-C₂-halogenoalkyl- orC₁-C₄-alkoxy-substituted C₃-C₈-cycloalkyl in which optionally onemethylene group is replaced by oxygen or sulphur or optionally halogen,C₁-C₄-alkyl-, C₁-C₄-alkoxy-, C₁-C₂-halogenoalkyl-,C₁-C₂-halogenoalkoxy-, cyano- or nitro-substituted phenyl, Q² representshydrogen or C₁-C₄-alkyl, or Q¹ and Q² together With the carbon atom toWhich they are attached represent optionally C₁-C₆-alkyl-, C₁-C₆-alkoxy-or C₁-C₂-halogenoalkyl-substituted C₃-C₇-cycloalkyl in which optionallyone ring member is replaced by oxygen or sulphur, with the proviso thatA and B do not form a further cycle, G represents hydrogen (a) orrepresents one of the groups

in which E represents a metal ion or an ammonium ion, L representsoxygen or sulphur and M represents oxygen or sulphur, R¹ represents ineach case optionally halogen-substituted C₁-C₂₀-alkyl, C₂-C₂₀-alkenyl,C₁-C₈-alkoxy-C₁-C₈-alkyl, C₁-C₈-alkylthio-C₁-C₈-alkyl,poly-C₁-C₈-alkoxy-C₁-C₈-alkyl or optionally halogen-, C₁-C₆-alkyl- orC₁-C₆-alkoxy-substituted C₃-C₈-cycloalkyl in which optionally one ormore not directly adjacent ring members are replaced by oxygen and/orsulphur, or represents optionally halogen-, cyano-, nitro-,C₁-C₆-alkyl-, C₁-C₆-alkoxy-, C₁-C₆-halogenoalkyl-,C₁-C₆-halogenoalkoxy-, C₁-C₆-alkylthio- orC₁-C₆-alkylsulphonyl-substituted phenyl, or represents optionallyhalogen-, nitro-, cyano-, C₁-C₆-alkyl-, C₁-C₆-alkoxy-,C₁-C₆-halogenoalkyl- or C₁-C₆-halogenoalkoxy-substitutedphenyl-C₁-C₆-alkyl, or represents optionally halogen-, C₁-C₆-alkyl- ortrifluoromethyl-substituted 5- or 6-membered hetaryl or representsoptionally halogen- or C₁-C₆-alkyl-substituted phenoxy-C₁-C₆-alkyl orrepresents optionally halogen-, amino- or C₁-C₆-alkyl-substituted 5- or6-membered hetaryloxy-C₁-C₆-alkyl, R² represents in each case optionallyhalogen-substituted C₁-C₂₀-alkyl, C₂-C₂₀-alkenyl,C₁-C₈-alkoxy-C₂-C₈-alkyl, poly-C₁-C₈-alkoxy-C₂-C₈-alkyl, or representsoptionally halogen-, C₁-C₆-alkyl- or C₁-C₆-alkoxy-substitutedC₃-C₈-cycloalkyl or represents in each case optionally halogen-, cyano-,nitro-, C₁-C₆-alkyl-, C₁-C₆-alkoxy-, C₁-C₆-halogenoalkyl- orC₁-C₆-halogenoalkoxy-substituted phenyl or benzyl, R³ representsoptionally halogen-substituted C₁-C₈-alkyl or represents in each caseoptionally halogen-, C₁-C₆-alkyl-, C₁-C₆-alkoxy-,C_(l)-C₄-halogenoalkyl-, C₁-C₄-halogenoalkoxy-, cyano- ornitro-substituted phenyl or benzyl, R⁴ and R⁵ independently of oneanother each represent in each case optionally halogen-substitutedC₁-C₈-alkyl, C₁-C₈-alkoxy, C₁-C₈-alkylamino, di-(C₁-C₈-alkyl)amino,C₁-C₈-alkylthio, C₂-C₈-alkenylthio, C₃-C₇-cycloalkylthilo or representin each case optionally halogen-, nitro-, cyano-, C₁-C₄-alkoxy-,C₁-C₄-halogenoalkoxy-, C₁-C₄-alkylthio-, C₁-C₄-halogenoalkylthio-,C₁-C₄-alkyl- or C₁-C₄-halogenoalkyl-substituted phenyl, benzyl, phenoxyor phenylthio, R⁶ and R⁷ independently of one another each representhydrogen, represent in each case optionally halogen-substitutedC₁-C₈-alkyl, C₃-C₈-cyclo-alkyl, C₁-C₈-alkoxy, C₃-C₈-alkenyl,C₁-C₈-alkoxy-C₁-C₈-alkyl, represent optionally halogen-,C₁-C₈-halogenoalkyl-, C₁-C₈-alkyl- or C₁-C₈-alkoxy-substituted phenyl,optionally halogen-, C₁-C₈-alkyl-, C₁-C₈-halogenoalkyl- orC₁-C₈-alkoxy-substituted benzyl or together represent an optionallyC₁-C₄-alkyl-substituted C₃-C₆-alkylene radical in which optionally onecarbon atom is replaced by oxygen or sulphur.
 3. Compounds of theformula (I) according to claim 1 in which W represents hydrogen,C₁-C₄-alkyl, chlorine or bromine, X represents chlorine, bromine,C₁-C₄-alkyl, C₁-C₄-alkoxy, C₂-C₃-alkenyl, ethinyl, C₁-C₂-halogenoalkyl,C₁-C₂-halogenoalkoxy or cyano, Y represents hydrogen, C₁-C₄-alkyl,C₁-C₂-halogenoalkyl, fluorine, chlorine, bromine, C₁-C₄-alkoxy,C₂-C₃-alkenyl, ethinyl, 2-thienyl, 3-thienyl or represents the radical

V¹ represents hydrogen fluorine, chlorine, bromine, C₁-C₆-alkyl,C₁-C₄-alkoxy, C₁-C₄-alkylthio, C₁-C₂-halogenoalkyl,C₁-C₂-halogeno-alkoxy, nitro, cyano or phenyl, V² represents hydrogen,fluorine, chlorine, C₁-C₄-alkyl, C₁-C₄-alkoxy or C₁-C₂-halogenoalkyl, Zrepresents hydrogen, fluorine, chlorine, bromine, C₁-C₄-alkyl,C₁-C₂-halogenoalkyl, C₁-C₄-alkoxy or C₁-C₂-halogenoalkoxy, with thefirst proviso that W, X and Z do not represent bromine, C₂-C₃-alkenyland ethinyl if Y represents V¹- and V²-substituted phenyl, 2-thienyl or3-thienyl and that secondly only one of the radicals X and Y representsC₂-C₃-alkenyl and ethinyl, with the proviso that in this case none ofthe other radicals W, X, Y and Z may represent bromine, A represents abond, hydrogen, in each case optionally fluorine-substitutedC₁-C₈-alkyl, C₁-C₄-alkoxy-C₁-C₂-alkyl, in each case optionallyfluorine-, chlorine-, methyl-, ethyl- or methoxy-substitutedC₅-C₆-cycloalkyl or C₃-C₆-cycloalkyl-C₁-C₂-alkyl in which optionally onering member is replaced by oxygen or sulphur or in each case optionallyfluorine-, chlorine-, bromine-, C₁-C₄-alkyl-, C₁-C₂-halogenoalkyl-,C₁-C₄-alkoxy- or C₁-C₂-halogenoalkoxy-substituted phenyl or benzyl, Brepresents hydrogen or C₁-C₄-alkyl, or A, B and the carbon atom to whichthey are attached represent saturated C₅-C₇-cycloalkyl in whichoptionally one ring member is replaced by oxygen and which is optionallymonosubstituted by C₁-C₄-alkyl, trifluoromethyl or C₁-C₄-alkoxy, withthe proviso that Q¹ and Q² do not form a further cycle, or B and Q¹together represent C₃-C₄-alkanediyl which is optionally monosubstitutedby C₁-C₂-alkyl and in which two not directly adjacent carbon atomsoptionally form a further five- or six-membered cycle, or Q¹ representshydrogen, hydroxyl, C₁-C₄-alkyl, C₁-C₄-alkoxy, C₁-C₄-alkoxy-C₁-C₂-alkyl,C₁-C₄-alkylacyloxy or optionally methyl- or methoxy-substitutedC₃-C₆-cycloalkyl in which optionally one methylene group is replaced byoxygen, Q² represents hydrogen, methyl or ethyl, or Q¹ and Q² togetherwith the carbon to which they are attached represent optionallyC₁-C₄-alkyl-, trifluoromethyl- or C₁-C₄-alkoxy-substituted saturatedC₅-C₆-cycloalkyl in which optionally one ring member is replaced byoxygen, with the proviso that A and B do not form a further cycle, Grepresents hydrogen (a) or represents one of the groups

in which E represents a metal ion or an ammonium ion, L representsoxygen or sulphur and M represents oxygen or sulphur, R¹ represents ineach case optionally fluorine- or chlorine-substituted C₁-C₁₆-alkyl,C₂-C₁₆-alkenyl, C₁-C₄-alkoxy-C₁-C₂-alkyl, C₁-C₄-alkylthio-C₁-C₂-alkyl,or optionally fluorine-, chlorine-, C₁-C₂-alkyl-, orC₁-C₂-alkoxy-substituted C₃-C₇-cycloalkyl in which optionally one or twonot directly adjacent ring members are replaced by oxygen and/orsulphur, or represents phenyl which is optionally mono- or disubstitutedby fluorine, chlorine, bromine, cyano, nitro, C₁-C₄-alkyl, C₁-C₄-alkoxy,trifluoromethyl or trifluoromethoxy, or represents pyridyl or thienyl,each of which is optionally monosubstituted by fluorine, chlorine,bromine, methyl, ethyl or trifluoromethyl, R² represents C₁-C₁₆-alkyl,C₂-C₁₆-alkenyl or C₁-C₄-alkoxy-C₂-C₄-alkyl, each of which is optionallymono- to trisubstituted by fluorine, or represents C₃-C₇-cycloalkylwhich is optionally monosubstituted by methyl, ethyl or methoxy, orrepresents phenyl or benzyl, each of which is optionally mono- ordisubstituted by fluorine, chlorine bromine cyano, nitro, C₁-C₄-alkyl,C₁-C₃-alkoxy, trifluoromethyl or trifluoromethoxy, R³ representsC₁-C₆-alkyl which is optionally mono- to pentasubstituted by fluorine orrepresents phenyl which is optionally mono- or disubstituted byfluorine, chlorine, bromine, C₁-C₄-alkyl, C₁-C₄-alkoxy, trifluoromethyl,trifluoromethoxy, cyano or nitro, R⁴ represents C₁-C₆-alkyl,C₁-C₆-alkoxy, C₁-C₆-alkylamino, di-(C₁-C₆-alkyl)amino, C₁-C₆-alkylthio,or represents phenyl, benzyl, phenoxy or phenylthio, each of which isoptionally mono- or disubstituted by fluorine, chlorine, bromine, nitro,cyano, C₁-C₃-alkoxy, trifluoromethoxy, C₁-C₃-alkyl or trifluoromethyl,R⁵ represents C₁-C₄-alkyl, C₁-C₄-alkoxy or C₁-C₄-alkylthio, R⁶represents C₁-C₆-alkyl, C₃-C₆-cycloalkyl, C₁-C₆-alkoxy, C₃-C₆-alkenyl,C₁-C₆-alkoxy-C₁-C₆-alkyl, or represents phenyl which is optionally mono-or disubstituted by fluorine, chlorine, bromine, trifluoromethyl,C₁-C₄-alkyl or C₁-C₄-alkoxy, or represents benzyl which is optionallymono- or disubstituted by fluorine, chlorine, bromine, methyl, ethyl,trifluoromethyl or methoxy, R⁷ represents hydrogen, C₁-C₆-alkyl orC₃-C₆-alkenyl, or R⁶ and R⁷ together represent a C₄-C₅-alkylene radicalwhich is optionally mono- or disubstituted by methyl or ethyl and inwhich optionally one methylene group is replaced by oxygen or sulphur.4. Compounds of the formula (I) according to claim 1, in which Wrepresents hydrogen, chlorine, bromine, methyl or ethyl, X representschlorine, bromine, methyl, ethyl, n-propyl, methoxy, ethoxy,trifluoromethyl, difluoromethoxy, trifluoromethoxy or cyano, Yrepresents hydrogen, methyl, ethyl, propyl, iso-propyl, fluorine,chlorine, bromine, methoxy or represents the radical

V¹ represents hydrogen, fluorine, chlorine, bromine, methyl, ethyl,iso-propyl, tert-butyl, methoxy, trifluoromethyl or trifluoromethoxy,cyano or phenyl, V² represents hydrogen, fluorine, chlorine, methyl,methoxy or trifluoromethyl, Z represents hydrogen, fluorine, chlorine,bromine, methyl, methoxy or trifluoromethyl, with the proviso that W, Xand Z do not represent bromine if Y represents V¹- and V²-substitutedphenyl, A represents a bond, hydrogen, methyl, ethyl, n-propyl,iso-propyl, n-butyl or iso-butyl, B represents hydrogen, methyl orethyl, or A, B and the carbon atoms to which they are attached representsaturated C₅-C₆-cycloalkyl in which optionally one ring member isreplaced by oxygen and which is optionally monosubstituted by methyl,ethyl, methoxy or ethoxy, with the proviso that Q¹ and Q² do not form afurther cycle or B and Q¹ together represent C₃-C₄-alkanediyl which isoptionally monosubstituted by methyl and in which two not directlyadjacent carbon atoms optionally form a further three- to six-memberedcycle, or Q¹ represents hydrogen, hydroxyl, methyl, ethyl, n-propyl,iso-propyl, methoxy, ethoxy, propoxy, acetyloxy or propionyloxy, Q²represents hydrogen, methyl or ethyl, or Q¹ and Q² together with thecarbon to which they are attached represent saturated C₆-cycloalkylwhich is optionally substituted by methyl, ethyl, methoxy, ethoxy,propoxy or butoxy and in which optionally one ring member is replaced byoxygen, with the proviso that A and B do not form a further cycle, Grepresents hydrogen (a) or represents one of the groups

in which E represents a metal ion or an ammonium ion, L representsoxygen or sulphur and M represents oxygen or sulphur, R¹ represents ineach case optionally fluorine- or chlorine-substituted C₁-C₈-alkyl,C₂-C₈-alkenyl, C₁-C₂-alkoxy-C₁-alkyl, C₁-alkylthio-C₁-alkyl,cyclopropyl, cyclopentyl or cyclohexyl or represents phenyl which isoptionally monosubstituted by fluorine, chlorine, bromine, cyano, nitro,methyl, ethyl, iso-propyl, tert-butyl, methoxy, trifluoromethyl ortrifluoromethoxy, or represents thienyl or pyridyl, each of which isoptionally monosubstituted by chlorine, bromine or methyl, R² representsC₁-C₈-alkyl, C₂-C₈-alkenyl or C₁-C₄-alkoxy-C₂-alkyl, or cyclohexyl orrepresents phenyl or benzyl, each of which is optionally monosubstitutedby fluorine, bromine, chlorine, cyano, nitro, methyl, tert-butyl,methoxy, trifluoromethyl or trifluoromethoxy, R³ represents methyl,ethyl, n-propyl, or phenyl which is optionally monosubstituted byfluorine, chlorine, bromine, methyl, tert-butyl, methoxy,trifluoromethyl, trifluoromethoxy, cyano or nitro, R⁴ representsC₁-C₄-alkyl, C₁-C₄-alkoxy, C₁-C₄-alkylamino, di-(C₁-C₄-alkyl)amino,C₁-C₄-alkylthio or represents phenyl, phenoxy or phenylthio, each ofwhich is optionally monosubstituted by fluorine, chlorine, bromine,nitro, cyano, C₁-C₂-alkoxy, trifluoromethoxy or C₁-C₃-alkyl, R⁵represents methyl, ethyl, methoxy, ethoxy, methylthio or ethylthio, R⁶represents C₁-C₄-alkyl, C₃-C₆-cycloalkyl, C₁-C₄-alkoxy, C₃-C₄-alkenyl,C₁-C₄-alkoxy-C₁-C₄-alkyl, R⁷ represents hydrogen, C₁-C₄-alkyl orC₃-C₄-alkenyl, or R⁶ and R⁷ together represent a C₆-alkylene racial inwhich optionally one methylene group is replaced by oxygen or sulphur.5. Compounds of the formula (I) according to claim 1, in which Wrepresents hydrogen, methyl, ethyl, chlorine or bromine, X representsmethyl, ethyl, n-propyl, trifluoromethyl or chlorine, Y representsmethyl, trifluoromethyl, chlorine, bromine, represents phenyl which isoptionally mono- or disubstituted by chlorine and/or methyl, Zrepresents hydrogen or methyl, with the proviso that W does notrepresent bromine if Y represents substituted phenyl, A representsmethyl, ethyl or a bond, B represents methyl or ethyl, or A and B andthe carbon atom to which they are attached represent cyclopropyl orcyclohexyl, or B and Q¹ together represent C₄-alkanediyl which isoptionally monosubstituted by methyl, Q¹ represents hydrogen, methyl,methoxy, ethoxy, propoxy, hydroxyl or acetyloxy, Q² represents hydrogenor methyl, G represents hydrogen (a) or represents one of the groups

where R¹ represents C₁-C₄-alkyl or represents phenyl or pyridyl, each ofwhich is optionally monosubstituted by chlorine, R² representsC₁-C₄-alkyl.
 6. Process for preparing compounds of the formula (I)according to claim 1, characterized in that to obtain (A) compounds ofthe formula (I-a)

in which A, B, Q¹, Q², W, X, Y and Z are each as defined above,compounds of the formula (II)

in which A, B, Q¹, Q², W, X, Y and Z are each as defined above, and R⁸represents alkyl, are condensed intramolecularly in the presence of adiluent and in the presence of a base; (B) compounds of the formulae(I-a) to (I-g)

in which A, B, G, Q¹, Q², W, X, Y and Z are each as defined above,compounds of the formulae (I-a′) to (I-g′),

in which A, B, R¹, R², R³, R⁴, R⁵, R⁶, R⁷, E, L, M, Q¹, Q², W′, X′, Y′and Z′ each have the meanings of W, X, Y and Z given above and where atleast one of the radicals W′, X′, Y′ represents chlorine, bromine oriodine, and Z′ does not represent bromine or iodine. α) are initiallyreacted with compounds of the formula (III)

in which R⁹ represents hydrogen and R¹⁰ represents C₁-C₄-alkyl orphenyl, in the presence of a solvent, a base and a catalyst, and thesilyl group is then removed, or β) are reacted with compounds of theformula (IV)

in which R⁹ represents hydrogen, methyl or ethyl and R¹⁰ representsC₁-C₄-alkyl, in the presence of a solvent, if appropriate in thepresence of a base and in the presence of a catalyst, or γ) in thespecific case where Y′ represents chlorine bromine or iodine and W′, X′and Z′ do not represent bromine or iodine, are reacted with boronicacids of the formula (V)

in which Y represents optionally substituted phenyl or hetaryl, in thepresence of a solvent, a base and a catalyst; (C) compounds of theformula (I-b) shown above in which A, B, Q¹, Q², R¹, W, X, Y and Z areeach as defined above, compounds of the formula (I-a) shown above inwhich A, B, Q¹, Q², W, X, Y and Z are each as defined above are in eachcase reacted (α) with compounds of the formula (VI)

in which R¹ is as defined above and Hal represents halogen or (B) withcompounds of the formula (VII) R¹—CO—O—CO—R¹   (VII) in which R¹ is asdefined above, if appropriate in the presence of a diluent and ifappropriate in the presence of an acid binder; (D) compounds of theformula (I-c) shown above in which A, B, Q¹, Q², R², M, W, X, Y and Zare each as defined above and L represents oxygen, compounds of theformula (I-a) shown above in which A, B, Q¹, Q², W, X, Y and Z are eachas defined above are in each case reacted with compounds of the formula(VIII) R²-M-CO—Cl   (VIII) in which R² and M are each as defined above,if appropriate in the presence of a diluent and if appropriate in thepresence of an acid binder; (E) compounds of the formula (I-c) shownabove in which A, B, Q¹, Q², R², M, W, X, Y and Z are each as definedabove and L represents sulphur, compounds of the formula (I-a) shownabove in which A, B, Q¹, Q², W, X, Y and Z are each as defined above,are in each case reacted with compounds of the formula (IX)

in which M and R² are each as defined above, if appropriate in thepresence of a diluent and if appropriate in the presence of an acidbinder and (F) compounds of the formula (I-d) shown above in which A, B,Q¹, Q², R³, W, X, Y and Z are each as defined above, compounds of theformula (I-a) shown above in which A, B, Q¹, Q², W, X, Y and Z are eachas defined above are in each case reacted with compounds of the formula(X) R³—SO₂—Cl   (X) in which R³ is as defined above, if appropriate inthe presence of a diluent and if appropriate in the presence of an acidbinder, (G) compounds of the formula (I-e) shown above in which A, B, L,Q¹, Q², R⁴, R⁵, W, X, Y and Z are each as defined above, compounds ofthe formula (I-a) shown above in which A, B, Q¹, Q², W, X, Y and Z areeach as defined above are in each case reacted with compounds of theformula (XI)

in which L, R⁴ and R⁵ are each as defined above and Hal representshalogen, if appropriate in the presence of a diluent and if appropriatein the presence of an acid binder, (H) compounds of the formula (I-f)shown above in which A, B, E, Q¹, Q², W, X, Y and Z are each as definedabove, compounds of the formula (I-a) shown above in which A, B, Q¹, Q²,W, X, Y and Z are each as defined above are in each case reacted withmetal compounds of amines of the formula (XII) or (XIII) Me(OR¹¹)_(t)  (XII)

in which Me represents a mono- or divalent metal, t represents thenumber 1 or 2 and R¹¹, R¹², R¹³ independently of one another eachrepresents hydrogen or alkyl, if appropriate in the presence of adiluent, (I) compounds of the formula (I-g) shown above in which A, B,L, Q¹, Q², R⁶, R⁷, W, X, Y and Z are each as defined above, compounds ofthe formula (I-a) shown above in which A, B, Q¹, Q², W, X, Y and Z areeach as defined above are in each case reacted (α) with compounds of theformula (XIV) R⁶—N═C=L   (XIV) in which R⁶ and L are each as definedabove, if appropriate in the presence of a diluent and if appropriate inthe presence of a catalyst or (β) with compounds of the formula (XV)

in which L, R⁶ and R⁷ are each as defined above, if appropriate in thepresence of a diluent and if appropriate in the presence of an acidbinder; J) compounds of the formula (XVI)

in which A and B are each as defined above and Alk represents alkylhaving 1 to 4 carbon atoms, are in each case reacted with compounds ofthe formula (XVII)

in which W, X, Y and Z are each as defined above and Hal representschlorine or bromine, if appropriate in the presence of a diluent or adiluent mixture and if appropriate in the presence of an acid binder. 7.Compounds of the formula (II)

in which A, B, Q¹, Q², W X, Y, Z and R⁸ are each as defined above. 8.Pesticides and herbicides, characterized in that they comprise at leastone compound of the formula (I) according to claim
 1. 9. Method forcontrolling animal pests and undesirable vegetation, characterized inthat compounds of the formula (I) according to claim 1 are allowed toact on pests and/or their habitat.
 10. Use of compounds of the formula(I) according to claim 1 for controlling animal pests and undesirablevegetation.
 11. Process for preparing pesticides and herbicides,characterized in that compounds of the formula (I) according to claim 1are mixed with extenders and/or surfactants.
 12. Use of compounds of theformula (I) according to claim 1 for preparing pesticides andherbicides.